Heterocyclic compound and organic light emitting element using same

ABSTRACT

The present application relates to a hetero-cyclic compound represented by Chemical Formula 1, and an organic light emitting device comprising the same.

TECHNICAL FIELD

This application claims priority to and the benefits of Korean PatentApplication No. 10-2016-0087507, filed with the Korean IntellectualProperty Office on Jul. 11, 2016, the entire contents of which areincorporated herein by reference.

The present application relates to a hetero-cyclic compound and anorganic light emitting device using the same.

BACKGROUND ART

An electroluminescent device is one type of self-emissive displaydevices, and has an advantage of having a wide viewing angle, and a highresponse speed as well as having an excellent contrast.

An organic light emitting device has a structure disposing an organicthin film between two electrodes. When a voltage is applied to anorganic light emitting device having such a structure, electrons andholes injected from the two electrodes bind and pair in the organic thinfilm, and light emits as these annihilate. The organic thin film may beformed in a single layer or a multilayer as necessary.

A material of the organic thin film may have a light emitting functionas necessary. For example, as a material of the organic thin film,compounds capable of forming a light emitting layer themselves may beused alone, or compounds capable of performing a role of a host or adopant of a host-dopant-based light emitting layer may also be used. Inaddition thereto, compounds capable of performing roles of holeinjection, hole transfer, electron blocking, hole blocking, electrontransfer, electron injection and the like may also be used as a materialof the organic thin film.

Development of an organic thin film material has been continuouslyrequired for enhancing performance, lifespan or efficiency of an organiclight emitting device.

PRIOR ART DOCUMENTS Patent Documents

U.S. Pat. No. 4,356,429

DISCLOSURE Technical Problem

The present application is directed to providing a novel hetero-cycliccompound and an organic light emitting device using the same.

Technical Solution

One embodiment of the present application provides a hetero-cycliccompound represented by the following Chemical Formula 1:

in Chemical Formula 1,

L1 is a direct bond; a substituted or unsubstituted C₆ to C₆₀ arylenegroup; or a substituted or unsubstituted C₂ to C₆₀ heteroarylene group,

Z1 is selected from the group consisting of hydrogen; deuterium; ahalogen group; —CN; a substituted or unsubstituted C₁ to C₆₀ alkylgroup; a substituted or unsubstituted C₆ to C₆₀ aryl group; asubstituted or unsubstituted C₂ to C₆₀ heteroaryl group; —SiRR′R″;—P(═O)RR′; and an amine group unsubstituted or substituted with a C₁ toC₂₀ alkyl group, a C₆ to C₆₀ aryl group or a C₂ to C₆₀ heteroaryl group,

m is an integer of 0 to 4,

n is an integer of 1 to 4,

R1 to R8 are the same as or different from each other, and eachindependently selected from the group consisting of hydrogen; deuterium;a halogen group; —CN; a substituted or unsubstituted C₁ to C₆₀ alkylgroup; a substituted or unsubstituted C₂ to Co alkenyl group; asubstituted or unsubstituted C₂ to C₆ alkynyl group; a substituted orunsubstituted C₁ to C₆₀ alkoxy group; a substituted or unsubstituted C₃to C₆₀ cycloalkyl group; a substituted or unsubstituted C₂ to C₆₀heterocycloalkyl group; a substituted or unsubstituted C₆ to C₆₀ arylgroup; a substituted or unsubstituted C₂ to C₆₀ heteroaryl group;—SiRR′R″; —P(═O)RR′; and an amine group unsubstituted or substitutedwith a C₁ to C₂₀ alkyl group, a C₆ to C₆₀ aryl group or a C₂ to C₆₀heteroaryl group, or two or more groups adjacent to each other bond toeach other to form a substituted or unsubstituted aliphatic or aromatichydrocarbon ring,

R, R′ and R″ are the same as or different from each other, and eachindependently hydrogen; deuterium; —CN; a substituted or unsubstitutedC₁ to C₆₀ alkyl group; a substituted or unsubstituted C₃ to C₆₀cycloalkyl group; a substituted or unsubstituted C₆ to C₆₀ aryl group;or a substituted or unsubstituted C₂ to C₆₀ heteroaryl group.

Another embodiment of the present application provides an organic lightemitting device comprising an anode, a cathode and one or more organicmaterial layers provided between the anode and the cathode, wherein oneor more layers of the organic material layers comprise the hetero-cycliccompound represented by Chemical Formula 1.

Advantageous Effects

A hetero-cyclic compound according to one embodiment of the presentapplication can be used as an organic material layer material of anorganic light emitting device. The hetero-cyclic compound can be used asa material of a hole injection layer, a hole transfer layer, a lightemitting layer, an electron transfer layer, an electron injection layer,a charge generation layer or the like in an organic light emittingdevice. Particularly, the hetero-cyclic compound represented by ChemicalFormula 1 can be used as a material of an electron transfer layer or acharge generation layer in an organic light emitting device. Inaddition, using the hetero-cyclic compound represented by ChemicalFormula 1 in an organic light emitting device lowers a driving voltageof the device, enhances light efficiency, and can enhance a lifespanproperty of the device with thermal stability of the compound.

DESCRIPTION OF DRAWINGS

FIG. 1 to FIG. 4 are diagrams each schematically illustrating alamination structure of an organic light emitting device according toone embodiment of the present application.

REFERENCE NUMERAL

-   -   100: Substrate    -   200: Anode    -   300: Organic Material Layer    -   301: Hole Injection Layer    -   302: Hole Transfer Layer    -   303: Light Emitting Layer    -   304: Hole Blocking Layer    -   305: Electron Transfer Layer    -   306: Electron Injection Layer    -   400: Cathode

Mode for Disclosure

Hereinafter, the present application will be described in detail.

A hetero-cyclic compound according to one embodiment of the presentapplication is represented by Chemical Formula 1. More specifically, thehetero-cyclic compound represented by Chemical Formula 1 is capable ofbeing used as an organic material layer material of an organic lightemitting device with such a core structure and structuralcharacteristics of substituents.

In one embodiment of the present application, when m of Chemical Formula1 is 2 or greater, two or more Lls may be the same as or different fromeach other. In addition, when n of Chemical Formula 1 is 2 or greater,two or more Zls may be the same as or different from each other.

In one embodiment of the present application, m of Chemical Formula 1may be an integer of 1 to 4.

In one embodiment of the present application, R1 and R2 of ChemicalFormula 1 may bond to each other to form a substituted or unsubstitutedaliphatic or aromatic hydrocarbon ring. In addition, in one embodimentof the present application, R3 and R4 of Chemical Formula 1 may bond toeach other to form a substituted or unsubstituted aliphatic or aromatichydrocarbon ring.

According to one embodiment of the present application, Chemical Formula1 may be represented by any one of the following Chemical Formulae 2 to7.

In Chemical Formulae 2 to 7,

R9 is represented by -(L2)p-(Z2)q,

L2 has the same definition as L1 of Chemical Formula 1 and Z2 has thesame definition as Z1 of Chemical Formula 1,

p is an integer of 0 to 3,

q is an integer of 1 to 4, and

R1 to R8 have the same definitions as in Chemical Formula 1.

In one embodiment of the present application, R5 to R8 of ChemicalFormula 1 may be each independently hydrogen or deuterium.

In one embodiment of the present application, L1 and L2 of ChemicalFormulae 1 to 7 are each independently a direct bond; a substituted orunsubstituted C₆ to C₆₀ arylene group; or a substituted or unsubstitutedC₂ to C₆₀ heteroarylene group.

In another embodiment, L1 and L2 of Chemical Formulae 1 to 7 are eachindependently a direct bond; a substituted or unsubstituted C₆ to C₄₀arylene group; or a substituted or unsubstituted C₂ to C₄₀ heteroarylenegroup.

In another embodiment, L1 and L2 of Chemical Formulae 1 to 7 are eachindependently a direct bond; a C₆ to C₄₀ arylene group; or a C₂ to C₄₀heteroarylene group.

In another embodiment, L1 and L2 of Chemical Formulae 1 to 7 may be eachindependently a direct bond; a phenylene group; a naphthylene group; apyrenylene group; a biphenylylene group; a triphenylenylene group; ananthracenylene group; a divalent pyridine group; a divalent pyrimidinegroup; a divalent triazine group; a divalent quinoline group; or adivalent pyrazine group.

In one embodiment of the present application, Z1 and Z2 of ChemicalFormulae 1 to 7 are each independently selected from the groupconsisting of hydrogen; deuterium; a substituted or unsubstituted C₆ toC₆₀ aryl group; a substituted or unsubstituted C₂ to C₆₀ heteroarylgroup; and —P(═O)RR′, and R and R′ are the same as or different fromeach other, and each independently hydrogen; deuterium; —CN; asubstituted or unsubstituted C₁ to C₆₀ alkyl group; a substituted orunsubstituted C₃ to C₆₀ cycloalkyl group; a substituted or unsubstitutedC₆ to C₆ aryl group; or a substituted or unsubstituted C₂ to C₆heteroaryl group.

In another embodiment, Z1 and Z2 of Chemical Formulae 1 to 7 are eachindependently selected from the group consisting of hydrogen; deuterium;a substituted or unsubstituted C₆ to C₄₀ aryl group; a substituted orunsubstituted C₂ to C₄₀ heteroaryl group; and —P(═O)RR′, and R and R′are the same as or different from each other, and each independentlyhydrogen; deuterium; or a substituted or unsubstituted C₆ to C₄₀ arylgroup.

In another embodiment, Z1 and Z2 of Chemical Formulae 1 to 7 are eachindependently selected from the group consisting of hydrogen; a C₆ toC₄₀ aryl group unsubstituted or substituted with one or moresubstituents selected from the group consisting of a C₆ to C₄₀ arylgroup, a C₂ to C₄₀ heteroaryl group and P(═O)RR′; a C₂ to C₄₀ heteroarylgroup unsubstituted or substituted with one or more substituentsselected from the group consisting of a C₆ to C₄₀ aryl group, a C₂ toC₄₀ heteroaryl group and P(═O)RR′; and —P(═O)RR′, and R and R′ are thesame as or different from each other and each independently a C₆ to C₄₀aryl group.

In another embodiment, Z1 and Z2 of Chemical Formulae 1 to 7 are eachindependently selected from the group consisting of hydrogen; a phenylgroup unsubstituted or substituted with one or more substituentsselected from the group consisting of a pyridine group, a quinolinegroup and P(═O)RR′; a naphthyl group unsubstituted or substituted withP(═O)RR′; an anthracene group unsubstituted or substituted with a phenylgroup; a pyrene group unsubstituted or substituted with one or moresubstituents selected from the group consisting of a pyridine group anda pyrimidine group; a fluoranthenyl group; a triphenylene groupunsubstituted or substituted with a pyrazine group; a biphenylene group;a fluorene group unsubstituted or substituted with one or moresubstituents selected from the group consisting of a phenyl group and axanthene group; a phenanthrene group and a spirobifluorene group, and Rand R′ are the same as or different from each other and eachindependently a phenyl group.

In another embodiment, Z1 and Z2 of Chemical Formulae 1 to 7 are eachindependently selected from the group consisting of hydrogen; a pyridinegroup unsubstituted or substituted with one or more substituentsselected from the group consisting of a phenyl group, a biphenyl groupand a pyridine group; a quinoline group unsubstituted or substitutedwith one or more substituents selected from the group consisting of apyridine group, a pyrimidine group and —P(═O)RR′; a phenanthroline groupunsubstituted or substituted with one or more substituents selected fromthe group consisting of a phenyl group and a pyridine group; apyrimidine group unsubstituted or substituted with one or moresubstituents selected from the group consisting of a phenyl group, abiphenyl group and a pyridine group; a quinazoline group; abenzimidazole group unsubstituted or substituted with a phenyl group; atriazine group unsubstituted or substituted with one or moresubstituents selected from the group consisting of a phenyl group and abiphenyl group; an indole group unsubstituted or substituted with aphenyl group; a carbazole group; a pyrido[2,3-b]indole groupunsubstituted or substituted with a pyridine group; aphenanthro[9,10-b]imidazole group unsubstituted or substituted with aphenyl group; and a pyrazine group unsubstituted or substituted with animidazo[1,2-a]pyridine group and a phenyl group, and R and R′ are thesame as or different from each other and each independently a phenylgroup.

In another embodiment, Z1 and Z2 of Chemical Formulae 1 to 7 may be eachindependently P(═O)RR′, and R and R′ are the same as or different fromeach other and each independently a phenyl group.

In one embodiment of the present application, R1 and R2 of ChemicalFormula 1 bond to each other to form an aromatic hydrocarbon ring, or R3and R4 bond to each other to form an aromatic hydrocarbon ring, and,among R1 to R4, groups that do not form the aromatic hydrocarbon ringmay be hydrogen or deuterium.

In another embodiment, R1 and R2 of Chemical Formula 1 bond to eachother to form a benzene ring, or R3 and R4 bond to each other to form abenzene ring, and, among R1 to R4, groups that do not form the benzenering may be hydrogen.

In one embodiment of the present application, R, R′ and R″ of ChemicalFormulae 1 to 7 are the same as or different from each other, and may beeach independently hydrogen; a substituted or unsubstituted C₁ to C₆₀alkyl group; or a substituted or unsubstituted C₆ to C₆₀ aryl group.

In the present specification, the term “substituted or unsubstituted”means being substituted with one or more substituents selected from thegroup consisting of deuterium; a halogen group; —CN; a C₁ to Co alkylgroup; a C₂ to C₆₀ alkenyl group; a C₂ to C₆₀ alkynyl group; a C₃ to C₆₀cycloalkyl group; a C₂ to C₆₀ heterocycloalkyl group; a C₆ to C₆₀ arylgroup; a C₂ to C₆₀ heteroaryl group; —SiRR′R″; —P(═O)RR′; a C₁ to C₂₀alkylamine group; a C₆ to C₆ arylamine group; and a C₂ to C₆₀heteroarylamine group, or being unsubstituted, or being substituted witha substituent bonding two or more of the above-mentioned substituents,or being substituted, or being substituted with a substituent linkingtwo or more substituents selected from among the above-mentionedsubstituents, or being unsubstituted. For example, “a substituentlinking two or more substituents” may comprise a biphenyl group. Inother words, a biphenyl group may be an aryl group, or may beinterpreted as a substituent linking two phenyl groups. The additionalsubstituents may be further substituted. R, R′ and R″ are the same as ordifferent from each other, and each independently hydrogen; deuterium;—CN; a substituted or unsubstituted C₁ to C₆₀ alkyl group; a substitutedor unsubstituted C₃ to C₆₀ cycloalkyl group; a substituted orunsubstituted C₆ to C₆₀ aryl group; or a substituted or unsubstituted C₂to C₆₀ heteroaryl group.

According to one embodiment of the present application, the “substitutedor unsubstituted” means being substituted with one or more substituentsselected from the group consisting of deuterium, a halogen group, —CN,SiRR′R″, P(═O)RR′, a C₁ to C₂₀ linear or branched alkyl group, a C₆ toC₆₀ aryl group, and a C₂ to C₆₀ heteroaryl group, or beingunsubstituted, and

R, R′ and R″ are the same as or different from each other, and eachindependently hydrogen; deuterium; —CN; a C₁ to C₆₀ alkyl groupunsubstituted or substituted with deuterium, a halogen group, —CN, a C₁to C₂₀ alkyl group, a C₆ to C₆₀ aryl group and a C₂ to C₆₀ heteroarylgroup; a C₃ to C₆₀ cycloalkyl group unsubstituted or substituted withdeuterium, halogen, —CN, a C₁ to C₂₀ alkyl group, a C₆ to C₆₀ aryl groupand a C₂ to C₆₀ heteroaryl group; a C₆ to C₆₀ aryl group unsubstitutedor substituted with deuterium, halogen, —CN, a C₁ to C₂₀ alkyl group, aC₆ to C₆₀ aryl group and a C₂ to C₆₀ heteroaryl group; or a C₂ to C₆₀heteroaryl group unsubstituted or substituted with deuterium, halogen,—CN, a C₁ to C₂₀ alkyl group, a C₆ to C₆₀ aryl group and a C₂ to C₆₀heteroaryl group.

The term “substituted” means a hydrogen atom bonding to a carbon atom ofa compound is changed to another substituent, and the position ofsubstitution is not limited as long as it is a position at which thehydrogen atom is substituted, that is, a position at which a substituentcan substitute, and when two or more substituents substitute, the two ormore substituents may be the same as or different from each other.

In the present specification, the halogen may be fluorine, chlorine,bromine or iodine.

In the present specification, the alkyl group comprises linear orbranched having 1 to 60 carbon atoms, and may be further substitutedwith other substituents. The number of carbon atoms of the alkyl groupmay be from 1 to 60, specifically from 1 to 40 and more specificallyfrom 1 to 20. Specific examples thereof may comprise a methyl group, anethyl group, a propyl group, an n-propyl group, an isopropyl group, abutyl group, an n-butyl group, an isobutyl group, a tert-butyl group, asec-butyl group, a 1-methyl-butyl group, a 1-ethyl-butyl group, a pentylgroup, an n-pentyl group, an isopentyl group, a neopentyl group, atert-pentyl group, a hexyl group, an n-hexyl group, a 1-methylpentylgroup, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a3,3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, ann-heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, acyclohexylmethyl group, an octyl group, an n-octyl group, a tert-octylgroup, a 1-methylheptyl group, a 2-ethylhexyl group, a 2-propylpentylgroup, an n-nonyl group, a 2,2-dimethylheptyl group, a 1-ethyl-propylgroup, a 1,1-dimethyl-propyl group, an isohexyl group, a 2-methylpentylgroup, a 4-methylhexyl group, a 5-methylhexyl group and the like, butare not limited thereto.

In the present specification, the alkenyl group comprises linear orbranched having 2 to 60 carbon atoms, and may be further substitutedwith other substituents. The number of carbon atoms of the alkenyl groupmay be from 2 to 60, specifically from 2 to 40 and more specificallyfrom 2 to 20. Specific examples thereof may comprise a vinyl group, a1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenylgroup, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a3-pentenyl group, a 3-methyl-1-butenyl group, a 1,3-butadienyl group, anallyl group, a 1-phenylvinyl-1-yl group, a 2-phenylvinyl-1-yl group, a2,2-diphenylvinyl-1-yl group, a 2-phenyl-2-(naphthyl-1-yl)vinyl-1-ylgroup, a 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, a stilbenyl group, astyrenyl group and the like, but are not limited thereto.

In the present specification, the alkynyl group comprises linear orbranched having 2 to 60 carbon atoms, and may be further substitutedwith other substituents. The number of carbon atoms of the alkynyl groupmay be from 2 to 60, specifically from 2 to 40 and more specificallyfrom 2 to 20.

In the present specification, the cycloalkyl group comprises monocyclicor multicyclic having 3 to 60 carbon atoms, and may be furthersubstituted with other substituents. Herein, the multicyclic means agroup in which the cycloalkyl group is directly linked to or fused withother cyclic groups. Herein, the other cyclic groups may be a cycloalkylgroup, however, may also be different types of cyclic groups such as aheterocycloalkyl group, an aryl group and a heteroaryl group. The numberof carbon groups of the cycloalkyl group may be from 3 to 60,specifically from 3 to 40 and more specifically from 5 to 20. Specificexamples thereof may comprise a cyclopropyl group, a cyclobutyl group, acyclopentyl group, a 3-methylcyclopentyl group, a2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexylgroup, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a3,4,5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, acycloheptyl group, a cyclooctyl group and the like, but are not limitedthereto.

In the present specification, the heterocycloalkyl group comprises O, S,Se, N or Si as a heteroatom, comprises monocyclic or multicyclic having2 to 60 carbon atoms, and may be further substituted with othersubstituents. Herein, the multicyclic means a group in which theheterocycloalkyl group is directly linked to or fused with other cyclicgroups. Herein, the other cyclic groups may be a heterocycloalkyl group,however, may also be different types of cyclic groups such as acycloalkyl group, an aryl group and a heteroaryl group. The number ofcarbon atoms of the heterocycloalkyl group may be from 2 to 60,specifically from 2 to 40 and more specifically from 3 to 20.

In the present specification, the aryl group comprises monocyclic ormulticyclic having 6 to 60 carbon atoms, and may be further substitutedwith other substituents. Herein, the multicyclic means a group in whichthe aryl group is directly linked to or fused with other cyclic groups.Herein, the other cyclic groups may be an aryl group, however, may alsobe different types of cyclic groups such as a cycloalkyl group, aheterocycloalkyl group and a heteroaryl group. The aryl group comprisesa spiro group. The number of carbon atoms of the aryl group may be from6 to 60, specifically from 6 to 40 and more specifically from 6 to 25.Specific examples of the aryl group may comprise a phenyl group, abiphenyl group, a triphenyl group, a naphthyl group, an anthryl group, achrysenyl group, a phenanthrenyl group, a perylenyl group, afluoranthenyl group, a triphenylenyl group, a phenalenyl group, apyrenyl group, a tetracenyl group, a pentacenyl group, a fluorenylgroup, an indenyl group, an acenaphthylenyl group, a benzofluorenylgroup, a spirobifluorenyl group, a 2,3-dihydro-1H-indenyl group, a fusedring thereof, and the like, but are not limited thereto.

In the present specification, the spiro group is a group comprising aspiro structure, and may have 15 to 60 carbon atoms. For example, thespiro group may comprise a structure in which a 2,3-dihydro-1H-indenegroup or a cyclohexane group spiro bonds to a fluorenyl group.Specifically, the following spiro group may comprise any one of thegroups having the following structural formulae.

In the present specification, the heteroaryl group comprises O, S, Se, Nor Si as a heteroatom, comprises monocyclic or multicyclic having 2 to60 carbon atoms, and may be further substituted with other substituents.Herein, the multicyclic means a group in which the heteroaryl group isdirectly linked to or fused with other cyclic groups. Herein, the othercyclic groups may be a heteroaryl group, however, may also be differenttypes of cyclic groups such as a cycloalkyl group, a heterocycloalkylgroup and an aryl group. The number of carbon atoms of the heteroarylgroup may be from 2 to 60, specifically from 2 to 40 and morespecifically from 3 to 25. Specific examples of the heteroaryl group maycomprise a pyridyl group, a pyrrolyl group, a pyrimidyl group, apyridazinyl group, a furanyl group, a thiophene group, an imidazolylgroup, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, athiazolyl group, an isothiazolyl group, a triazolyl group, a furazanylgroup, an oxadiazolyl group, a thiadiazolyl group, a dithiazolyl group,a tetrazolyl group, a pyranyl group, a thiopyranyl group, a diazinylgroup, an oxazinyl group, a thiazinyl group, a dioxynyl group, axanthene group, a triazinyl group, a tetrazinyl group, a quinolyl group,an isoquinolyl group, a quinazolinyl group, an isoquinazolinyl group, aqninozolinyl group, a naphthyridyl group, an acridinyl group, aphenanthridinyl group, an imidazopyridinyl group, a diazanaphthalenylgroup, a triazaindene group, an indolyl group, an indolizinyl group, abenzothiazolyl group, a benzoxazolyl group, a benzimidazolyl group, abenzothiophene group, a benzofuran group, a dibenzothiophene group, adibenzofuran group, a carbazolyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a phenazinyl group, a dibenzosilole group,spirobi(dibenzosilole), a dihydrophenazinyl group, a phenoxazinyl group,a phenanthridyl group, an imidazopyridinyl group, a thienyl group, anindolo[2,3-a]carbazolyl group, an indolo[2,3-b]carbazolyl group, anindolinyl group, a 10,11-dihydro-dibenzo[b,f]azepine group, a9,10-dihydroacridinyl group, a phenanthrazinyl group, aphenothiathiazinyl group, a phthalazinyl group, a naphthylidinyl group,a phenanthrolinyl group, a phenanthro[9,10-d]imidazole group, abenzo[c][1,2,5]thiadiazolyl group, a5,10-dihydrobenzo[b,e][1,4]azasilinyl, a pyrazolo[1,5-c]quinazolinylgroup, a pyrido[2,3-b]indole group, a pyrido[1,2-b]indazolyl group, apyrido[1,2-a]imidazo[1,2-e]indolinyl group, an imidazo[1,2-a]pyridinegroup, a 5,11-dihydroindeno[1,2-b]carbazolyl group and the like, but arenot limited thereto.

In the present specification, the amine group may be selected from thegroup consisting of a monoalkylamine group; a monoarylamine group; amonoheteroarylamine group; —NH₂; a dialkylamine group; a diarylaminegroup; a diheteroarylamine group; an alkylarylamine group; analkylheteroarylamine group; and an arylheteroarylamine group, andalthough not particularly limited thereto, the number of carbon atoms ispreferably from 1 to 30. Specific examples of the amine group maycomprise a methylamine group, a dimethylamine group, an ethylaminegroup, a diethylamine group, a phenylamine group, a naphthylamine group,a biphenylamine group, a dibiphenylamine group, an anthracenylaminegroup, a 9-methyl-anthracenylamine group, a diphenylamine group, aphenylnaphthylamine group, a ditolylamine group, a phenyltolylaminegroup, a triphenylamine group, a biphenylnaphthylamine group, aphenylbiphenylamine group, a biphenylfluorenylamine group, aphenyltriphenylenylamine group, a biphenyltriphenylenylamine group andthe like, but are not limited thereto.

In the present specification, the arylene group means the aryl grouphaving two bonding sites, that is, a divalent group. Descriptions on thearyl group provided above may be applied thereto except for each being adivalent. In addition, the heteroarylene group means the heteroarylgroup having two bonding sites, that is, a divalent group. Descriptionson the heteroaryl group provided above may be applied thereto except foreach being a divalent.

According to one embodiment of the present application, Chemical Formula1 may be represented by any one of the following compounds, but is notlimited thereto.

In addition, by introducing various substituents to the structure ofChemical Formula 1, compounds having unique properties of the introducedsubstituents may be synthesized. For example, by introducingsubstituents normally used as hole injection layer materials, holetransfer layer materials, light emitting layer materials, electrontransfer layer materials and charge generation layer materials used formanufacturing an organic light emitting device to the core structure,materials satisfying conditions required for each organic material layermay be synthesized.

In addition, by introducing various substituents to the structure ofChemical Formula 1, the energy band gap may be finely controlled, andmeanwhile, properties at interfaces between organic materials areenhanced, and material applications may become diverse.

Meanwhile, the hetero-cyclic compound has excellent thermal stabilitywith a high glass transition temperature (Tg). Such an increase in thethermal stability becomes an important factor in providing drivingstability to a device.

The hetero-cyclic compound according to one embodiment of the presentapplication may be prepared through a multistep chemical reaction. Someintermediate compounds are prepared first, and the compound of ChemicalFormula 1 may be prepared from the intermediate compounds. Morespecifically, the hetero-cyclic compound according to one embodiment ofthe present application may be prepared based on preparation examples tobe described below.

Another embodiment of the present application provides an organic lightemitting device comprising the hetero-cyclic compound represented byChemical Formula 1.

The organic light emitting device according to one embodiment of thepresent application may be manufactured using common organic lightemitting device manufacturing methods and materials except that one ormore organic material layers are formed using the hetero-cyclic compounddescribed above.

The hetero-cyclic compound may be formed into an organic material layerthrough a solution coating method as well as a vacuum deposition methodwhen manufacturing the organic light emitting device. Herein, thesolution coating method means spin coating, dip coating, inkjetprinting, screen printing, a spray method, roll coating and the like,but is not limited thereto.

Specifically, the organic light emitting device according to oneembodiment of the present application comprises an anode, a cathode, andone or more organic material layers provided between the anode and thecathode, wherein one or more layers of the organic material layerscomprise the hetero-cyclic compound represented by Chemical Formula 1.

FIGS. 1 to 3 illustrate a lamination order of electrodes and organicmaterial layers of an organic light emitting device according to oneembodiment of the present application. However, the scope of the presentapplication is not limited to these diagrams, and structures of organiclight emitting devices known in the art may also be used in the presentapplication.

FIG. 1 illustrates an organic light emitting device in which an anode(200), an organic material layer (300) and a cathode (400) areconsecutively laminated on a substrate (100). However, the structure isnot limited to such a structure, and as illustrated in FIG. 2, anorganic light emitting device in which a cathode, an organic materiallayer and an anode are consecutively laminated on a substrate may alsobe obtained.

FIG. 3 illustrates a case of the organic material layer being amultilayer. The organic light emitting device according to FIG. 3comprises a hole injection layer (301), a hole transfer layer (302), alight emitting layer (303), a hole blocking layer (304), an electrontransfer layer (305) and an electron injection layer (306). However, thescope of the present application is not limited to such a laminationstructure, and as necessary, other layers except the light emittinglayer may not be included, and other necessary functional layers may befurther included.

In addition, the organic light emitting device according to oneembodiment of the present application comprises an anode, a cathode, andtwo or more stacks provided between the anode and the cathode, whereinthe two or more stacks each independently comprise a light emittinglayer, a charge generation layer is included between the two or morestacks, and the charge generation layer comprises the hetero-cycliccompound represented by Chemical Formula 1.

In addition, the organic light emitting device according to oneembodiment of the present application comprises an anode, a first stackprovided on the anode and comprising a first light emitting layer, acharge generation layer provided on the first stack, a second stackprovided on the charge generation layer and comprising a second lightemitting layer, and a cathode provided on the second stack. Herein, thecharge generation layer may comprise the hetero-cyclic compoundrepresented by Chemical Formula 1. In addition, the first stack and thesecond stack may each independently further comprise one or more typesof the hole injection layer, the hole transfer layer, the hole blockinglayer, the electron transfer layer, the electron injection layerdescribed above and the like.

The charge generation layer may be an N-type charge generation layer,and the charge generation layer may further comprise a dopant known inthe art in addition to the hetero-cyclic compound represented byChemical Formula 1.

As the organic light emitting device according to one embodiment of thepresent application, an organic light emitting device having a 2-stacktandem structure is schematically illustrated in FIG. 4.

Herein, the first electron blocking layer, the first bole blockinglayer, the second hole blocking layer and the like described in FIG. 4may not be included in some cases.

The organic light emitting device according to the present specificationmay be manufactured using materials and methods known in the art exceptthat one or more layers of the organic material layers comprise thehetero-cyclic compound represented by Chemical Formula 1.

The hetero-cyclic compound represented by Chemical Formula 1 may formone or more layers of the organic material layers of the organic lightemitting device alone. However, as necessary, the hetero-cyclic compoundrepresented by Chemical Formula 1 may be mixed with other materials toform the organic material layers.

The hetero-cyclic compound represented by Chemical Formula 1 may be usedas a material of the charge generation layer in the organic lightemitting device.

The hetero-cyclic compound represented by Chemical Formula 1 may be usedas a material of the electron transfer layer, the hole blocking layer,the light emitting layer or the like in the organic light emittingdevice. As one example, the hetero-cyclic compound represented byChemical Formula 1 may be used as a material of the electron transferlayer, the hole transfer layer or the light emitting layer in theorganic light emitting device.

In addition, the hetero-cyclic compound represented by Chemical Formula1 may be used as a material of the light emitting layer in the organiclight emitting device. As one example, the hetero-cyclic compoundrepresented by Chemical Formula 1 may be used as a phosphorescent hostmaterial of the light emitting layer in the organic light emittingdevice.

In the organic light emitting device according to one embodiment of thepresent application, materials other than the hetero-cyclic compound ofChemical Formula 1 are illustrated below, however, these are forillustrative purposes only and not for limiting the scope of the presentapplication, and may be replaced by materials known in the art.

As the anode material, materials having relatively large work functionmay be used, and transparent conductive oxides, metals, conductivepolymers or the like may be used. Specific examples of the anodematerial comprise metals such as vanadium, chromium, copper, zinc andgold, or alloys thereof; metal oxides such as zinc oxide, indium oxide,indium tin oxide (ITO) and indium zinc oxide (IZO); combinations ofmetals and oxides such as ZnO:Al or SnO₂:Sb; conductive polymers such aspoly(3-methylcompound), poly[3,4-(ethylene-1,2-dioxy)compound](PEDT),polypyrrole and polyaniline, but are not limited thereto.

As the cathode material, materials having relatively small work functionmay be used, and metals, metal oxides, conductive polymers or the likemay be used. Specific examples of the cathode material comprise metalssuch as magnesium, calcium, sodium, potassium, titanium, indium,yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloysthereof; multilayer structure materials such as LiF/Al or LiO₂/Al, andthe like, but are not limited thereto.

As the hole injection material, known hole injection materials may beused, and for example, phthalocyanine compounds such as copperphthalocyanine disclosed in U.S. Pat. No. 4,356,429, or starburst-typeamine derivatives such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA),4,4′,4″-tri[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA) or1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB)described in the literature [Advanced Material, 6, p. 677 (1994)],polyaniline/dodecylbenzene sulfonic acid,poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate),polyaniline/camphor sulfonic acid orpolyaniline/poly(4-styrene-sulfonate) that are conductive polymershaving solubility, and the like, may be used.

As the hole transfer material, pyrazoline derivatives, arylamine-basedderivatives, stilbene derivatives, triphenyldiamine derivatives and thelike may be used, and low molecular or high molecular materials may alsobe used.

As the electron transfer material, metal complexes of oxadiazolederivatives, anthraquinodimethane and derivatives thereof, benzoquinoneand derivatives thereof, naphthoquinone and derivatives thereof,anthraquinone and derivatives thereof, tetracyanoanthraquinodimethaneand derivatives thereof, fluorenone derivatives, diphenyldicyanoethyleneand derivatives thereof, diphenoquinone derivatives, 8-hydroxyquinolineand derivatives thereof, and the like, may be used, and high molecularmaterials may also be used as well as low molecular materials.

As examples of the electron injection material, LiF is typically used inthe art, however, the present application is not limited thereto.

As the light emitting material, red, green or blue light emittingmaterials may be used, and as necessary, two or more light emittingmaterials may be mixed and used. In addition, fluorescent materials mayalso be used as the light emitting material, however, phosphorescentmaterials may also be used.

As the light emitting material, materials emitting light by bondingelectrons and holes injected from an anode and a cathode, respectively,may be used alone, however, materials having a host material and adopant material involved in light emission together may also be used.

The organic light emitting device according to one embodiment of thepresent application may be a top-emission type, a bottom-emission typeor a dual-emission type depending on the materials used.

The hetero-cyclic compound according to one embodiment of the presentapplication may also be used in an organic electronic device comprisingan organic solar cell, an organic photo conductor, an organic transistorand the like under a similar principle used in the organic lightemitting device.

Hereinafter, the present specification will be described in more detailwith reference to examples, however, these are for illustrative purposesonly, and the scope of the present application is not limited thereto.

EXAMPLE <Preparation Example 1> Preparation of Compound 10

1) Preparation of (MSAIm)Cl

A 1-methyl-1H-imidazole compound (2 g, 24.36 mmol) was dissolved in 50ml of MC. Chlorosulfonic acid (1.6 ml, 24.36 mmol) was added dropwisethereto at 0° C., the temperature was raised to room temperature, andthe result was stirred for 1 hour. The reaction solution was washedtwice with dichloromethane to obtain target Compound (MSAIm)Cl (3.2 g,67%).

2) Preparation of Compound 10-1

After dissolving a naphtylamine compound (16.2 g, 112.91 mmol) in 200 mlof EtOH, 4-bromobenzaldehyde (19 g, 102.64 mmol), 1H-indene-1,3(2H)-dione (15 g, 102.64 mmol) and (MSAIm)Cl (1 g, 5.13 mmol) were addedthereto, and the result was stirred under reflux. Excess EtOH was addedthereto, and the result was ultrasonic treated and filtered to obtaintarget Compound 10-1 (42 g, 85%).

3) Preparation of Compound 10-2

500 ml of MC was introduced to Compound 10-1 (42 g, 95.82 mmol) anddispersed. MnO₂ (142 g, 1633.31 mmol) was added thereto, and the resultwas stirred for 24 hours at room temperature. Solids were filtered, andthe filtrate was concentrated and recrystallized with MC/MeOH to obtaintarget Compound 10-2 (13 g, 31%).

4) Preparation of Compound 10-3

After dissolving Compound 10-2 (13 g, 29.80 mmol) in 400 ml of DEG,hydrazine monohydrate (95.5 g, 2979.60 mmol) was added thereto, and theresult was stirred under reflux. KOH (16.7 g, 297.96 mmol) dissolved in80 ml of D.W was added dropwise thereto, and the result was stirred at140° C. 1 L of D.W was added thereto for precipitation and the resultwas filtered, washed with D.W and MeOH, and then dried to obtain targetCompound 10-3 (11.5 g, 91%).

5) Preparation of Compound 10-4

After dissolving Compound 10-3 (11 g, 26.05 mmol) in 150 ml of THF,KOt-Bu (8.8 g, 78.14 mmol) was added thereto at 0° C., and the resultwas stirred for 10 minutes. Iodomethane (11.1 g, 78.14 mmol) was addedthereto, and the result was stirred at room temperature. D.W was addedthereto, the result was extracted with MC, and the MC layer was driedwith anhydrous Na₂SO₄.

The result was purified using column chromatography with EA and hexaneas a developing solvent to obtain target Compound 10-4 (9 g, 77%).

6) Preparation of Compound 10-5

After dissolving Compound 10-4 (9.2 g, 20.43 mmol) in 200 ml of1,4-dioxane, bis(pinacolato)diboron (7.8 g, 30.64 mmol), PdCl₂(dppf)(0.8 g, 1.02 mmol) and potassium acetate (8 g, 81.71 mmol) were addedthereto, and the result was stirred under reflux. D.W was added thereto,the result was extracted with MC, and the MC layer was dried withanhydrous Na₂SO₄. The result was purified using column chromatographywith EA and hexane as a developing solvent to obtain target Compound10-5 (10 g, 98%).

7) Preparation of Compound 10

After introducing Compound 10-5 (11.2 g, 22.52 mmol) and 1-bromopyrene(5.7 g, 20.26 mmol) to 100 ml of toluene, 20 ml of EtOH and 20 ml ofD.W, Pd(PPh₃)₄ (1.3 g, 1.13 mmol) and K₂CO₃ (6.2 g, 45.03 mmol) wereadded thereto, and the result was stirred under reflux. D.W was addedthereto, the result was extracted with MC, and the MC layer was driedwith anhydrous Na₂SO₄. After vacuum concentrating the solvent, MeOH wasadded thereto to recrystallize and obtain solids. The result waspurified using column chromatography with EA and hexane as a developingsolvent to obtain target Compound 10 (7.9 g, 61%).

Target Compound A was synthesized in the same manner as the preparationof Compound 10 except that, in Preparation Example 1, Intermediate A ofthe following Table 1 was used instead of 1-bromopyrene.

TABLE 1 Compound Number Intermediate A Target Compound A Yield 1

55% 6

50% 13

61% 14

60% 15

54% 27

59% 32

64% 34

62% 44

51% 53

58% 65

57% 72

55% 77

50% 80

50% 110

55% 113

51% 117

57% 120

61% 124

59% 128

53% 130

63% 138

51% 146

50% 155

54% 160

55% 162

59% 164

57%

<Preparation Example 2> Preparation of Compound 179

1) Preparation of Compound 179-1

After dissolving an aniline compound (10.4 g, 112.91 mmol) in 200 ml ofEtOH, 4-bromobenzaldehyde (19 g, 102.64 mmol), 1H-indene-1,3(2H)-dione(15 g, 102.64 mmol) and (MSAIm)Cl (1 g, 5.13 mmol) were added thereto,and the result was stirred under reflux. Excess EtOH was added thereto,and the result was ultrasonic treated and filtered to obtain targetCompound 179-1 (42 g, 85%).

2) Preparation of Compound 179-2

500 ml of MC was introduced to Compound 179-1 (37 g, 95.82 mmol) anddispersed. MnO₂ (142 g, 1633.31 mmol) was added thereto, and the resultwas stirred for 24 hours at room temperature. Solids were filtered, andthe filtrate was concentrated and recrystallized with MC/MeOH to obtaintarget Compound 179-2 (13 g, 31%).

3) Preparation of Compound 179-3

After dissolving Compound 179-2 (11.5 g, 29.80 mmol) in 400 ml of DEG,hydrazine monohydrate (95.5 g, 2979.60 mmol) was added thereto, and theresult was stirred under reflux. KOH (16.7 g, 297.96 mmol) dissolved in80 ml of D.W was added dropwise thereto, and the result was stirred at140° C. 1 L of D.W was added thereto for precipitation and the resultwas filtered, washed with D.W and MeOH, and then dried to obtain targetCompound 179-3 (11.5 g, 91%).

4) Preparation of Compound 179-4

After dissolving Compound 179-3 (9.6 g, 26.05 mmol) in 150 ml of THF,KOt-Bu (8.8 g, 78.14 mmol) was added thereto at 0° C., and the resultwas stirred for 10 minutes. Iodomethane (11.1 g, 78.14 mmol) was addedthereto, and the result was stirred at room temperature. D.W was addedthereto, the result was extracted with MC, and the MC layer was driedwith anhydrous Na₂SO₄.

The result was purified using column chromatography with EA and hexaneas a developing solvent to obtain target Compound 179-4 (9 g, 77%).

5) Preparation of Compound 179-5

After dissolving Compound 179-4 (9.7 g, 20.43 mnmol) in 200 ml of1,4-dioxane, bis(pinacolato)diboron (7.8 g, 30.64 mmol), PdCl₂(dppf)(0.8 g, 1.02 mmol) and potassium acetate (8 g, 81.71 mmol) were addedthereto, and the result was stirred under reflux. D.W was added thereto,the result was extracted with MC, and the MC layer was dried withanhydrous Na₂SO₄. The result was purified using column chromatographywith EA and hexane as a developing solvent to obtain target Compound179-5 (10 g, 98%).

6) Preparation of Compound 179

After introducing Compound 179-5 (11.2 g, 22.52 mmol) and2-bromo-1,10-phenanthroline (5.3 g, 20.26 mmol) to 100 ml of toluene, 20ml of EtOH and 20 ml of D.W, Pd(PPh₃)₄ (1.3 g, 1.13 mmol) and K₂CO₃ (6.2g, 45.03 mmol) were added thereto, and the result was stirred underreflux. D.W was added thereto, the result was extracted with MC, and theMC layer was dried with anhydrous Na₂SO₄. After vacuum concentrating thesolvent, MeOH was added thereto to recrystallize and obtain solids. Theresult was purified using column chromatography with EA and hexane as adeveloping solvent to obtain target Compound 179 (7.1 g, 57%).

Target Compound B was synthesized in the same manner as the preparationof Compound 179 except that, in Preparation Example 2, Intermediate B ofthe following Table 2 was used instead of 2-bromo-1,10-phenanthroline.

TABLE 2 Compound Number Intermediate B Target Compound B Yield 171

50% 174

58% 178

49% 184

55% 195

48% 196

60% 208

58% 211

55% 218

46% 224

40% 226

40% 280

51% 284

56% 290

55% 298

50% 303

45% 316

57% 320

55% 323

57% 329

60% 332

58%

<Preparation Example 3> Preparation of Compound 337

1) Preparation of Compound 337-1

After dissolving a naphthalen-2-amine compound (10.4 g, 112.91 mmol) in200 ml of EtOH, 4-bromo-1-naphthaldehyde (23 g, 102.64 mmol),1H-indene-1,3(2H)-dione (15 g, 102.64 mmol) and (MSAIm)Cl (1 g, 5.13mmol) were added thereto, and the result was stirred under reflux.Excess EtOH was added thereto, and the result was ultrasonic treated andfiltered to obtain target Compound 337-1 (42 g, 85%).

2) Preparation of Compound 337-2

500 ml of MC was introduced to Compound 337-1 (37 g, 95.82 mmol) anddispersed. MnO₂ (142 g, 1633.31 mmol) was added thereto, and the resultwas stirred for 24 hours at room temperature. Solids were filtered, andthe filtrate was concentrated and recrystallized with MC/MeOH to obtaintarget Compound 337-2 (13 g, 31%).

3) Preparation of Compound 337-3

After dissolving Compound 337-2 (11.5 g, 29.80 mmol) in 400 ml of DEG,hydrazine monohydrate (95.5 g, 2979.60 mmol) was added thereto, and theresult was stirred under reflux. KOH (16.7 g, 297.96 mmol) dissolved in80 ml of D.W was added dropwise thereto, and the result was stirred at140° C. 1 L of D.W was added thereto for precipitation and the resultwas filtered, washed with D.W and MeOH, and then dried to obtain targetCompound 337-3 (11.5 g, 91%).

4) Preparation of Compound 337-4

After dissolving Compound 337-3 (9.6 g, 26.05 mmol) in 150 ml of THF,KOt-Bu (8.8 g, 78.14 mmol) was added thereto at 0° C., and the resultwas stirred for 10 minutes. Iodomethane (11.1 g, 78.14 mmol) was addedthereto, and the result was stirred at room temperature. D.W was addedthereto, the result was extracted with MC, and the MC layer was driedwith anhydrous Na₂SO₄.

The result was purified using column chromatography with EA and hexaneas a developing solvent to obtain target Compound 337-4 (9 g, 77%).

5) Preparation of Compound 337-5

After dissolving Compound 337-4 (9.7 g, 20.43 mmol) in 200 ml of1,4-dioxane, bis(pinacolato)diboron (7.8 g, 30.64 mmol), PdCl₂(dppf)(0.8 g, 1.02 mmol) and potassium acetate (8 g, 81.71 mmol) were addedthereto, and the result was stirred under reflux. D.W was added thereto,the result was extracted with MC, and the MC layer was dried withanhydrous Na₂SO₄. The result was purified using column chromatographywith EA and hexane as a developing solvent to obtain target Compound337-5 (10 g, 98%).

6) Preparation of Compound 337

After introducing Compound 337-5 (11.2 g, 22.52 mmol) and4-bromo-2,6-diphenylpyrimidine (6.3 g, 20.26 mmol) to 100 ml of toluene,20 ml of EtOH and 20 ml of D.W, Pd(PPh₃)₄ (1.3 g, 1.13 mmol) and K₂CO₃(6.2 g, 45.03 mmol) were added thereto, and the result was stirred underreflux. D.W was added thereto, the result was extracted with MC, and theMC layer was dried with anhydrous Na₂SO₄. After vacuum concentrating thesolvent, MeOH was added thereto to recrystallize and obtain solids. Theresult was purified using column chromatography with EA and hexane as adeveloping solvent to obtain target Compound 337 (6.5 g, 68%).

Target Compound C was synthesized in the same manner as the preparationof Compound 337 except that, in Preparation Example 3, Intermediate C ofthe following Table 3 was used instead of4-bromo-2,6-diphenylpyrimidine.

TABLE 3 Compound Number Intermediate C Target Compound C Yield 357

50% 360

58% 361

49%

Target Compound D was synthesized in the same manner as the preparationof Compound 337 except that, in the synthesis of 366-1 in PreparationExample 3, Synthesis Reagent D of the following Table 4 was used insteadof the synthesis reagent 4-bromo-1-naphthaldehyde.

TABLE 4 Compound Number Synthesis Reagent D Target Compound D Yield 341

55% 349

49%

<Preparation Example 4> Preparation of Compound 400

1) Preparation of Compound 400-1

After dissolving a naphthalen-1-amine compound (17.3 g, 112.91 mmol) in200 ml of EtOH, 4-bromo-1-naphthaldehyde (23 g, 102.64 mmol),1H-indene-1,3(2H)-dione (15 g, 102.64 mmol) and (MSAIm)Cl (1 g, 5.13mmol) were added thereto, and the result was stirred under reflux.Excess EtOH was added thereto, and the result was ultrasonic treated andfiltered to obtain target Compound 400-1 (42 g, 85%).

2) Preparation of Compound 400-2

500 ml of MC was introduced to Compound 400-1 (37 g, 95.82 mmol) anddispersed. MnO₂ (142 g, 1633.31 mmol) was added thereto, and the resultwas stirred for 24 hours at room temperature. Solids were filtered, andthe filtrate was concentrated and recrystallized with MC/MeOH to obtaintarget Compound 400-2 (13 g, 31%).

3) Preparation of Compound 400-3

After dissolving Compound 400-2 (11.5 g, 29.80 mmol) in 400 ml of DEG,hydrazine monohydrate (95.5 g, 2979.60 mmol) was added thereto, and theresult was stirred under reflux. KOH (16.7 g, 297.96 mmol) dissolved in80 ml of D.W was added dropwise thereto, and the result was stirred at140° C. 1 L of D.W was added thereto for precipitation and the resultwas filtered, washed with D.W and MeOH, and then dried to obtain targetCompound 400-3 (11.5 g, 91%).

4) Preparation of Compound 400-4

After dissolving Compound 400-3 (9.6 g, 26.05 mmol) in 150 ml of THF,KOt-Bu (8.8 g, 78.14 mmol) was added thereto at 0° C., and the resultwas stirred for 10 minutes. Iodomethane (11.1 g, 78.14 mmol) was addedthereto, and the result was stirred at room temperature. D.W was addedthereto, the result was extracted with MC, and the MC layer was driedwith anhydrous Na₂SO₄.

The result was purified using column chromatography with EA and hexaneas a developing solvent to obtain target Compound 400-4 (9 g, 77%).

5) Preparation of Compound 400-5

After dissolving Compound 400-4 (9.7 g, 20.43 mmol) in 200 ml of1,4-dioxane, bis(pinacolato)diboron (7.8 g, 30.64 mmol), PdCl₂(dppf)(0.8 g, 1.02 mmol) and potassium acetate (8 g, 81.71 mmol) were addedthereto, and the result was stirred under reflux. D.W was added thereto,the result was extracted with MC, and the MC layer was dried withanhydrous Na₂SO₄. The result was purified using column chromatographywith EA and hexane as a developing solvent to obtain target Compound400-5 (10 g, 98%).

6) Preparation of Compound 400

After introducing Compound 400-5 (11.2 g, 22.52 mmol) and2-(4-bromophenyl)-9-phenyl-1,10-phenanthroline (6.3 g, 20.26 mmol) to100 ml of toluene, 20 ml of EtOH and 20 ml of D.W, Pd(PPh₃)₄ (1.3 g,1.13 mmol) and K₂CO₃ (6.2 g, 45.03 mmol) were added thereto, and theresult was stirred under reflux. D.W was added thereto, the result wasextracted with MC, and the MC layer was dried with anhydrous Na₂SO₄.After vacuum concentrating the solvent, MeOH was added thereto torecrystallize and obtain solids. The result was purified using columnchromatography with EA and hexane as a developing solvent to obtaintarget Compound 400 (7.1 g, 68%).

Target Compound E was synthesized in the same manner as the preparationof Compound 400 except that, in Preparation Example 4, Intermediate E ofthe following Table 5 was used instead of2-(4-bromophenyl)-9-phenyl-1,10-phenanthroline.

TABLE 5 Compound Number Intermediate E target Compound E Yield 392

50% 395

58% 399

49% 401

44% 402

38%

Compounds were prepared in the same manner as in the preparationexamples, and the synthesis identification results are shown in Table 6and Table 7. Table 6 shows measurement values of ¹H NMR (CDCl₃, 200MHz), and Table 7 shows measurement values of field desorption massspectrometry (FD-MS).

TABLE 6 Example ¹H NMR (CDCl₃, 200 Mz) 1 δ = 8.54(d, 1H), 8.01-7.99(t,3H), 7.86(d, 1H), 7.75(d, 2H), 7.61-7.37(m, 7H), 7.27(t, 1H), 7.25(m,4H), 1.69(s, 6H) 6 δ = 8.54(d, 1H), 8.26(s, 1H), 8.20(s, 1H),8.09~7.99(m, 5H), 7.86(d, 1H), 7.71(t, 1H), 7.61~7.53(m, 3H), 7.37(t,2H), 7.27(t, 1H), 7.25(d, 4H), 1.69(s, 6H) 10 δ = 8.54(d, 1H), 8.31(d,1H), 8.15(d, 1H), 8.08~7.86(m, 9H), 7.70(d, 1H), 7.61~7.53(m, 2H),7.39~7.37(t, 2H), 7.27(t, 1H), 7.25(d, 4H), 1.69(s, 6H) 13 δ = 8.80(d,1H), 8.71~8.69(t, 3H), 8.54(d, 1H), 8.45(d, 1H), 8.20(d, 1H),8.01~7.99(t, 3H), 7.90~7.86(d, 2H), 7.61~7.53(m, 3H), 7.39~7.37(t, 2H),7.29~2.25(m, 4H), 1.69(s, 6H) 14 δ = 8.71~8.69(d, 4H), 8.54(d, 1H),8.33(d, 2H), 8.20(d, 1H), 8.01~7.99(t, 3H), 7.90~7.86(d, 2H),7.61~7.49(m, 5H), 7.39~7.37(t, 2H), 7.29~7.25(m, 5H), 1.69(s, 6H) 15 δ =8.80(d, 1H), 8.67(d, 1H), 8.54~8.44(m, 3H), 8.01~7.99(t, 3H), 7.86(d,1H), 7.62~7.53(m, 4H), 7.39~7.27(m, 3H), 7.25(d, 4H), 1.69(s, 6H) 27 δ =8.65(d, 1H), 8.54~8.51(t, 2H), 8.39(d, 1H), 8.30(d, 1H), 8.15~8.14(t,2H), 8.01~7.99(m, 3H), 7.89~7.86(d, 2H), 7.61~7.53(m, 2H), 7.39~7.27(m,4H), 7.25(d, 4H), 7.17(t, 1H), 1.69(s, 6H) 32 δ = 9.18(d, 2H), 9.14(s,2H), 8.55~8.54(d, 3H), 8.01(m, 3H), 7.86(d, 1H), 7.74(t, 2H),7.61~7.53(m, 2H), 7.39~7.37(m, 2H), 7.27~7.23(m, 6H), 1.69(s, 6H) 34 δ =9.24(s, 1H), 8.70(d, 1H), 8.54(d, 1H), 8.42(d, 1H), 8.01~7.99(m, 3H),7.86(d, 1H), 7.61~7.53(m, 3H), 7.39~7.37(m, 2H), 7.25(d, 8H), 1.69(s,6H) 44 δ = 8.54(d, 2H), 8.36(d, 4H), 8.01~7.96(m, 5H), 7.86(d, 1H),7.61~7.50(m, 8H), 7.39~7.37(t, 2H), 7.27~7.25(m, 3H), 1.69(s, 6H) 53 δ =8.85(s, 2H), 8.67(s, 2H), 8.54~8.49(d, 3H), 8.39(d, 2H), 8.04~7.99(m,10H), 7.86(d, 1H), 7.61~7.53(m, 8H), 7.39~7.31(t, 2H), 7.27~7.25(m, 5H),1.69(s, 6H) 65 δ = 9.24(s, 1H), 8.70(d, 1H), 8.54(d, 1H), 8.42(d, 1H),8.01~7.94(m, 4H), 7.86(d, 1H), 7.73(t, 1H), 7.61~7.53(m, 5H),7.39~7.37(t, 2H), 7.27~7.20(m, 5H), 1.69(s, 6H) 72 δ = 8.69~8.71(d, 2H),8.54(d, 1H), 8.33(d, 4H), 8.01~7.94(m, 4H), 7.86(d, 1H), 7.73(t, 1H),7.61~7.22(m, 20H), 1.69(s, 6H) 77 δ = 9.24(s, 1H), 8.70(d, 1H),8.54~8.52(d, 2H), 8.42(d, 1H), 8.28(d, 1H), 8.15(d, 2H), 8.01~7.86(m,7H), 7.70~7.53(m, 8H), 7.39~7.37(t, 2H), 7.27~7.25(m, 5H), 1.69(s, 6H)80 δ = 9.18(d, 2H), 8.54(d, 1H), 8.41~8.35(m, 3H), 8.01~7.94(m, 4H),7.86(d, 1H), 7.74~7.71(m, 3H), 7.61~7.53(t, 4H), 7.39~7.23(m, 10H),1.69(s, 6H) 110 δ = 8.54(d, 1H), 8.01~7.99(m, 6H), 7.86(d, 2H),7.61~7.53(m, 4H), 7.39~7.37(m, 4H), 7.27~7.20(m, 10H), 1.69(s, 6H) 113 δ= 9.27(s, 1H), 9.00(d, 2H), 8.79(d, 1H), 8.54(d, 1H), 8.37~8.30(m, 4H),8.01~7.99(t, 3H), 7.86(d, 1H), 7.70~7.53(m, 9H), 7.39~7.37(m, 4H),7.27~7.25(m, 5H), 1.69(s, 6H) 117 δ = 9.08~9.00(d, 3H), 8.84~8.79(d,2H), 8.25(d, 1H), 8.05~7.99(m, 4H), 7.90~7.86(d, 2H), 7.70~7.53(m, 8H),7.39~7.37(t, 4H), 7.27~7.25(d,5H), 1.69(s, 6H) 120 δ = 9.00(d, 2H),8.73(d, 2H), 8.54(d, 1H), 8.01~7.86(m, 5H), 7.86~7.83(d, 1H),7.61~7.53(m, 4H), 7.39~7.7.35(m, 4H), 7.27~7.25(m, 8H), 1.69(s, 6H) 124δ = 9.02~8.90(d, 2H), 8.54(d, 1H), 8.23(s, 1H), 8.01~7.84(m, 10H),7.75~7.70(d, 2H), 7.61~7.37(m, 12H), 7.27~7.25(d, 7H), 1.69(s, 6H) 128 δ= 9.15(s, 1H), 8.54~8.51(d, 2H), 8.36~8.30(d, 4H), 8.01~7.86(m, 6H),7.61~7.50(m, 9H), 7.39~7.37(t, 3H), 7.27~7.25(d, 5H), 1.69(s, 6H) 130 δ= 8.54~8.52(d, 2H), 8.23(s, 1H), 8.01~7.86(m, 11H), 7.75(d, 2H),7.61~7.39(m, 12H), 7.27~7.25(m, 7H), 1.69(s, 6H) 138 δ = 8.73~8.70(d,2H), 8.54~8.50(d, 1H), 8.22~8.19(d, 4H), 8.01~7.99(t, 3H), 7.86(d, 1H),7.61~7.37(m, 8H), 7.27~7.20(6H), 1.69(s, 6H) 146 δ = 9.18(d, 1H),8.70~8.65(d, 3H), 8.54(d, 1H), 8.45~8.43(d, 1H), 8.35~8.31(t, 3H),8.09~7.94(m, 6H), 7.88~7.86(d, 2H), 7.78~7.74(t, 1H), 7.61~7.53(t, 2H),7.39~7.23(m, 7H), 1.69(s, 6H) 155 δ = 9.62~9.60(d, 1H), 9.27~9.24(d,2H), 9.13~9.11(d, 1H), 8.81~8.79(d, 1H), 8.72~8.70(d, 1H), 8.54~8.51(d,1H), 8.46~8.30(m, 5H), 8.01~7.99(d, 3H), 7.87~7.85(d, 1H), 7.70~7.53(m,5H), 7.39~7.37(t, 2H), 7.25~7.22(d, 4H), 1.69(s, 6H) 160 δ =8.54~8.51(d, 1H), 8.10~8.08(d, 1H), 8.01~7.99(d, 3H), 7.90~7.86(d, 3H),7.79~7.77(d, 1H), 7.61~7.53(t, 3H), 7.38~7.14(m, 15H), 7.03~7.00(t, 2H),1.69(s, 6H) 171 δ = 8.09~7.99(m, 5H), 7.89~7.86(d, 1H), 7.63~7.51(m,5H), 7.39~7.37(t, 3H), 7.27~2.25(d, 5H), 1.69(s, 6H) 174 δ = 8.85(s,1H), 8.67(s, 1H), 8.49(s, 1H), 8.39~8.87(d, 1H), 8.08~8.01(d, 4H),7.89~7.86(d, 1H), 7.62~7.51(m, 5H), 7.39~7.37(t, 2H), 7.27~7.25(d, 5H),1.69(s, 6H) 178 δ = 8.71~8.69(d, 2H), 8.52~8.50(d, 1H), 8.28~8.26(d,1H), 8.15~7.87(m, 9H), 7.70~7.62(t, 3H), 7.51~7.49(t, 1H), 7.39~7.37(t,2H), 7.27~7.25(d, 5H), 1.69(s, 6H) 179 δ = 8.80~8.79(d, 1H),8.71~8.69(t, 3H), 8.45~8.42(d, 1H), 8.20~8.18(d, 1H), 8.08~8.01(d, 2H),7.90~7.87(d, 2H), 7.62~7.51(m, 3H), 7.39~7.37(t, 2H), 7.29~7.25(t, 4H),1.69(s, 6H) 184 δ = 9.27(s, 1H), 8.79~8.77(d, 1H), 8.37~8.33(m, 4H),8.08~8.01(d, 2H), 7.87~7.85(d, 1H), 7.70~7.62(m, 5H), 7.52~7.50(t, 2H),7.39~7.34(t, 2H), 7.27~7.25(d, 5H), 1.69(s, 6H) 195 δ = 8.09~8.08(d,2H), 8.01~8.00(d, 1H), 7.90~7.87(t, 5H), 7.78~7.86(d, 1H), 7.62~7.37(m,8H), 7.28~7.19(m, 10H), 1.69(s, 6H) 196 δ = 8.08~8.06(d, 1H),8.01~7.87(m, 4H), 7.63~7.51(m, 7H), 7.39~7.27(m, 6H), 6.5~6.62(t, 1H),5.83~5.79(d, 2H), 3.69(t, 1H), 3.16(d, 1H), 2.5(d 1H), 1.69(s, 6H) 208 δ= 8.35~8.28(m, 6H), 8.23(s, 1H), 8.08~8.01(d, 2H), 7.87~7.82(d, 3H),7.75~7.70(d, 2H), 7.62~7.58(t, 1H), 7.51~7.37(m, 9H), 7.27~7.20(t, 3H),1.69(s, 6H) 211 δ = 8.23(s, 1H), 8.08~7.87(m, 9H), 7.62~7.49(m, 8H),7.39~7.30(t, 2H), 7.27~7.20(t, 3H), 1.69(s, 6H) 218 δ = 8.09~7.99(m,11H), 7.87~7.84(d, 1H), 7.63~7.51(m, 8H), 7.39~7.30(t, 4H), 7.27~7.20(m, 5H), 1.69(s, 6H) 224 δ = 8.82(s, 1H), 8.80(d, 2H), 8.71~8.68(d,2H), 8.45~8.40(t, 4H), 8.20~8.15(d, 2H), 8.08~8.01(d, 2H), 7.87~7.84(d,1H), 7.62~7.51(m, 4H), 7.39~7.34(t, 2H), 7.27~7.10(m, 5H), 1.69(s, 6H)226 δ = 8.81~8.79(d, 1H), 8.67~8.64(d, 2H), 8.50~8.40(m, 4H),8.08~8.05(d, 1H), 8.02(s, 3H), 8.01~7.98(d, 1H), 7.87~7.84(d, 1H),7.62~7.51(m, 6H), 7.39~7.25(m, 9H), 1.69(s, 6H) 280 δ = 9.00~8.95(d,2H), 8.52~8.49(d, 1H), 8.31~8.28(d, 1H), 8.15~8.01(m, 7H), 7.92~7.87(d,2H), 7.70~7.61(m, 4H), 7.51~7.48(t, 1H), 7.39~7.33(m, 4H), 1.69(s, 6H)284 δ = 9.00~8.95(d, 2H), 8.42~8.39(d, 2H), 8.10~8.01(m, 4H),7.87~7.83(d, 1H), 7.76~7.73(d, 1H), 7.67~7.58(t, 5H), 7.51~7.48(t, 2H),7.39~7.31(m, 5H), 7.27~7.25(d, 5H), 1.69(s, 6H) 298 δ = 9.02~8.99(d,1H), 8.95~8.92(d, 1H), 8.23(s, 1H), 8.08~7.87(m, 9H), 7.75~7.70(d, 2H),7.62~7.37(m, 12H), 7.27~7.20(m, 7H), 1.69(s, 6H) 303 δ = 8.23(s, 1H),8.22~8.19(d, 4H), 8.08~7.87(m, 7H), 7.62~7.37(m, 14H), 7.27~7.20(t, 5H),1.69(s, 6H) 316 δ = 9.60~9.57(d, 1H), 9.27(s, 1H), 9.11~9.07(d, 1H),8.79~8.71(d, 3H), 8.46~8.43(d, 2H), 8.30~8.26(d, 1H), 8.15~8.01(m, 3H),7.87~7.83(d, 1H), 7.70~7.62(t, 3H), 7.51~7.49(d, 1H), 7.39~7.34(t, 2H),7.27~7.22(t, 6H), 1.69(s, 6H) 320 δ = 9.90~9.88(d, 1H), 9.27(s, 1H),9.11~9.08(d, 1H), 8.91~8.88(d, 1H), 8.79~8.72(d, 1H), 8.48~8.33(m, 6H),8.08~8.01(d, 3H), 7.88~7.82(d, 2H), 7.70~7.51(m, 5H), 7.39~7.24(m, 6H),1.69(s, 6H) 323 δ = 9.60~9.57(d, 1H), 9.27(s, 1H), 9.11~9.08(d, 1H),8.79~7.74(d, 1H), 8.46~8.30(m, 4H), 8.08~8.00(d, 2H), 7.94(s, 1H),7.87~7.84(d, 1H), 7.75~7.60(m, 8H), 7.51~7.30(m, 6H), 7.27~7.22(d, 5H),1.69(s, 6H) 329 δ = 8.08~8.02(d, 1H), 8.01~7.90(m, 5H), 7.87~7.80(d,1H), 7.77~7.70(d, 4H), 7.62~7.56(t, 1H), 7.51~7.40(m, 7H), 7.39~7.30(t,2H), 7.27~7.20(m, 5H), 1.69(s, 6H) 332 δ = 8.48~8.40(d, 1H),8.30~8.20(t, 3H), 8.08~7.97(d, 2H), 7.87~7.80(d, 1H), 7.62~7.48(t, 3H),7.39~7.30(d, 2H), 7.27~7.15(t, 4H), 6.86~6.79(t, 1H), 1.69(s, 6H) 337 δ= 8.97(d, 2H), 8.29(d, 1H), 8.35(d, 2H), 8.29(d, 2H), 8.23(s, 1H),8.01~7.94(m, 5H), 7.86(d, 1H), 7.61~7.49(m, 10H), 7.39(t, 2H), 7.27(t,1H), 1.69(s, 6H) 341 δ = 8.54(d, 1H), 8.46(s, 1H), 8.35~8.30(d, 4H),8.23(s, 1H), 8.01~7.85(m, 9H), 7.75~7.54(m, 4H), 7.53~7.37(m, 10H),7.27(t, 1H), 1.69(s, 6H) 349 δ = 8.54(d, 1H), 8.20(d, 4H), 8.01~7.86(m,8H), 7.61~7.49(m, 14H), 7.27(t, 1H), 1.69(s, 6H) 357 δ = 9.08~8.79(t,3H), 8.95~8.70(t, 2H), 8.06(d, 1H), 8.05~7.99(m, 5H), 7.90~7.80(d, 3H),7.68~7.30(m, 10H), 7.20(t,1H), 1.69(s, 6H) 360 δ = 9.02(d, 1H), 8.95(d,1H), 8.73(d, 2H), 8.54(d, 1H), 8.06~7.88(m, 6H), 7.86~7.80(d, 2H),7.53~7.37(m, 6H), 7.27~7.20(m, 5H), 1.69(s, 6H) 361 δ = 9.02~8.95(d,2H), 8.80(d, 1H), 8.67(d, 1H), 8.50~8.44(d, 3H), 8.06~7.99(m, 4H),7.86~7.77(d, 2H), 7.62~7.27(m, 10H), 1.69(s, 6H) 392 δ = 8.56~8.51(d,2H), 8.11~7.90(m, 5H), 7.81(d, 1H), 7.72~7.37(m, 11H), 7.27~7.20(m, 8H),1.69(s, 6H) 395 δ = 9.02(d, 1H), 8.95(d, 1H), 8.80(d, 1H), 8.71(d, 1H),8.51(d, 1H), 8.45(d, 2H), 8.20(d, 1H), 8.11~8.01(t, 3H), 7.90(d, 1H),7.84(d, 1H), 7.72~7.60(m, 3H), 7.56(t, 1H), 7.52~7.39(m, 4H),7.29~7.27(t, 2H), 7.25(d, 4H), 1.69(s, 6H) 399 δ = 9.02(d, 1H), 8.95(d,1H), 8.51(d, 1H), 8.35(d, 2H), 8.23(s, 1H), 8.11~7.94(m, 6H), 7.84(d,1H), 7.72~7.61(t, 3H), 7. 400 δ = 9.26(s, 2H), 9.08(d, 1H), 8.84(d, 1H),8.51(d, 1H), 8.17(d, 1H), 8.11(d, 1H), 8.08~8.01(t, 3H), 7.90(d, 1H),7.72~7.62(m, 8H), 7.39(t, 2H), 7.27(t, 1H), 7.25(d, 4H), 1.69(s, 6H) 401δ = 9.02(d, 1H), 8.95(d, 1H), 8.51(d, 1H), 8.35(d, 2H), 8.23(s, 1H),8.11~7.94(m, 6H), 7.84(d, 1H), 7.72~7.63(t, 3H), 7.55~7.37(m, 10H),7.27~7.25(d, 5H), 1.69(s, 6H) 402 δ = 9.26(s, 2H), 9.08(d, 1H), 8.84(d,1H), 8.51(d, 1H), 8.17~8.05(m, 5H), 7.90(d, 1H), 7.72~7.62(m, 7H),7.39~7.30(t, 2H), 7.27(t, 1H), 7.25(d, 4H), 1.69(s, 6H)

TABLE 7 Compound FD-Mass Compound FD-Mass 1 m/z = 447.58(C34H25N =447.21) 2 m/z = 448.56(C33H24N2 = 448.44) 3 m/z = 448.56(C33H24N2 =448.32) 4 m/z = 448.56(C33H24N2 = 448.51) 5 m/z = 497.64(C38H27N =497.51) 6 m/z = 498.62(C37H26N2 = 498.59) 7 m/z = 498.62(C37H26N2 =498.54) 8 m/z = 547.70(C42H29N = 547.51) 9 m/z = 699.89(C54H37N =699.81) 10 m/z = 571.73(C44H29N = 571.70) 11 m/z = 648.80(C49H32N2 =648.77) 12 m/z = 648.80(C49H32N2 = 648.65) 13 m/z = 549.67(C40H27N3 =549.44) 14 m/z = 625.77(C40H31N3 = 625.31) 15 m/z = 549.67(C40H27N3 =549.45) 16 m/z = 701.87(C52H35N3 = 701.66) 17 m/z = 571.72(C44H29N =571.21) 18 m/z = 597.76(C46H31N = 597.44) 19 m/z = 449.55(C32H23N3 =449.31) 20 m/z = 498.62(C37H26N3 = 498.55) 21 m/z = 547.70(C42H29N =547.49) 22 m/z = 701.87(C52H35N3 = 701.28) 23 m/z = 602.74(C43H30N4 =602.24) 24 m/z = 678.83(C49H34N4 = 678.27) 25 m/z = 754.93(C55H38N4 =754.30) 26 m/z = 754.93(C55H38N4 = 754.31) 27 m/z = 614.75(C44H30N4 =614.24) 28 m/z = 687.88(C53H37N = 687.29) 29 m/z = 685.87(C53H35N =685.27) 30 m/z = 564.73(C42H32N2 = 564.21) 31 m/z = 537.66(C39H27N3 =537.22) 32 m/z = 602.74(C43H30N4 = 602.40) 33 m/z = 524.66(C39H28N2 =524.21) 34 m/z = 524.68(C39H28N2 = 524.31) 35 m/z = 524.66(C39H28N2 =524.33) 36 m/z = 574.72(C43H30N2 = 574.61) 37 m/z = 574.72(C43H30N2 =574.55) 38 m/z = 625.77(C46H31N3 = 625.49) 39 m/z = 701.87(C52H35N3 =701.68) 40 m/z = 625.77(C46H31N3 = 625.51) 41 m/z = 777.99(C58H39N3 =777.88) 42 m/z = 677.85(C50H85N3 = 677.53) 43 m/z = 601.75(C44H31N3 =601.59) 44 m/z = 602.74(C43H30N4 = 602.60) 45 m/z = 601.75(C44H31N3 =602.64) 46 m/z = 601.75(C44H31N3 = 601.43) 47 m/z = 601.75(C44H31N3 =601.21) 48 m/z = 601.75(C44H31N3 = 601.39) 49 m/z = 701.87(C52H35N3 =701.44) 50 m/z = 701.87(C52H35N3 = 701.52) 51 m/z = 599.77(C46H33N =599.64) 52 m/z = 699.89(C54H37N = 699.82) 53 m/z = 800.01(C62H41N =800.00) 54 m/z = 1104.40(C86H57N = 1104.21) 55 m/z = 848.06(C66H41N =848.01) 56 m/z = 1002.23(C76H47N = 1002.11) 57 m/z = 1002.23(C76H47N3 =1002.10) 58 m/z = 803.96(C58H37N5 = 803.21) 59 m/z = 956.16(C70H45N5 =956.01) 60 m/z = 803.96(C58H37N5 = 803.77) 61 m/z = 1108.36(C82H53N5 =1108.19) 62 m/z = 601.75(C44H31N3 = 601.22) 63 m/z = 523.67(C40H29N =523.41) 64 m/z = 524.66(C39H28N2 = 524.39) 65 m/z = 524.66(C39H28N2 =524.52) 66 m/z = 524.66(C39H28N2 = 524.38) 67 m/z = 574.72(C43H30N2 =574.11) 68 m/z = 574.72(C43H30N2 = 574.69) 69 m/z = 625.77(C46H31N3 =625.47) 70 m/z = 701.87(C52H35N3 = 701.55) 71 m/z = 625.77(C46H31N3 =625.28) 72 m/z = 777.97(C58H39N3 = 777.85) 73 m/z = 573.73(C44H31N =573.64) 74 m/z = 623.79(C48H33N = 623.40) 75 m/z = 775.99(C60H41N =775.85) 76 m/z = 647.82(C50H33N = 647.77) 77 m/z = 724.90(C55H36N2 =724.60) 78 m/z = 724.90(C55H36N2 = 724.88) 79 m/z = 701.87(C52H35N3 =775.81) 80 m/z = 779.94(C56H37N5 = 779.30) 81 m/z = 677.85(C50H35N3 =677.43) 82 m/z = 601.75(C44H31N3 = 601.47) 83 m/z = 602.74(C43H30N4 =602.22) 84 m/z = 678.83(C49H34N4 = 678.27) 85 m/z = 677.85(C50H35N3 =677.68) 86 m/z = 602.74(C43H30N4 = 601.30) 87 m/z = 678.83(C39H34N4 =678.27) 88 m/z = 536.67(C40H28N2 = 536.47) 89 m/z = 524.66(C39H28N2 =524.51) 90 m/z = 524.66(C39H28N2 = 524.25) 91 m/z = 524.66(C39H28N2 =524.33) 92 m/z = 574.72(C43H30N2 = 574.40) 93 m/z = 574.72(C43H30N2 =574.61) 94 m/z = 625.77(C46H31N3 = 625.28) 95 m/z = 701.87(C52H35N3 =701.39) 96 m/z = 625.77(C46H31N3 = 625.44) 97 m/z = 777.97(C58H39N3 =777.31) 98 m/z = 523.67(C40H29N = 523.58) 99 m/z = 524.66(C39H28N2 =524.20) 100 m/z = 524.66(C39H28N2 = 524.29) 101 m/z = 524.66(C39H28N2 =524.38) 102 m/z = 574.72(C43H30N2 = 574.19) 103 m/z = 574.72(C43H30N2 =574.10) 104 m/z = 625.77(C46H31N3 = 625.70) 105 m/z = 701.87(C52H35N3 =701.24) 106 m/z = 625.77(C46H31N3 = 625.44) 107 m/z = 777.97(C58H39N3 =777.87) 108 m/z = 639.80(C47H33N3 = 639.25) 109 m/z = 639.80(C47H33N3 =639.42) 110 m/z = 740.95(C56H40N2 = 740.48) 111 m/z = 740.95(C56H40N2 =740.89) 112 m/z = 675.83(C50H33N3 = 675.26) 113 m/z = 723.91(C56H37N =723.29) 114 m/z = 699.89(C54H37N = 699.29) 115 m/z = 574.72(C43H30N2 =574.24) 116 m/z = 575.71(C42H29N3 = 575.23) 117 m/z = 673.85(C52H35N =673.27) 118 m/z = 697.88(C54H35N = 697.27) 119 m/z = 624.78(C47H32N2 =624.25) 120 m/z = 651.81(C48H33N3 = 651.26) 121 m/z = 651.81(C48H33N3 =651.26) 122 m/z = 699.89(C54H37N = 699.29) 123 m/z = 701.87(C52H35N3 =701.28) 124 m/z = 804.00(C60H41N3 = 803.33) 125 m/z = 727.91(C54H37N3 =727.29) 126 m/z = 624.78(C47H32N2 = 624.25) 127 m/z = 573.73(C44H31N =573.24) 128 m/z = 728.89(C53H36N4 = 728.29) 129 m/z = 804.00(C60H41N3 =803.33) 130 m/z = 804.00(C60H41N3 = 803.33) 131 m/z = 7804.00(C60H41N3 =803.33) 132 m/z = 804.99(C59H40N4 = 804.32) 133 m/z = 880.10(C66H45N3 =879.36) 134 m/z = 879.11(C67H46N2 = 878.36) 135 m/z = 880.10(C66H45N3 =879.36) 136 m/z = 881.09(C65H44N4 = 880.35) 137 m/z = 777.98(C58H39N3 =777.31) 138 m/z = 625.77(C48H31N3 = 625.25) 139 m/z = 625.77(C46H31N3 =625.25) 140 m/z = 701.87(C52H35N3 = 701.28) 141 m/z = 701.87(C52H35N3 =701.28) 142 m/z = 701.87(C52H35N3 = 701.28) 143 m/z = 625.77(C46H31N3 =625.25) 144 m/z = 525.65(C38H27N3 = 525.22) 145 m/z = 576.70(C41H28N4 =576.23) 146 m/z = 702.86(C51H34N3 = 702.27) 147 m/z = 649.79(C48H31N3 =649.25) 148 m/z = 771.96(C60H37N = 771.29) 149 m/z = 625.77(C46H31N3 =625.25) 150 m/z = 675.83(C50H33N3 = 675.26) 151 m/z = 675.83(C50H33N3 =675.26) 152 m/z = 724.90(C55H36N2 = 724.28) 153 m/z = 724.90(C55H36N2 =724.28) 154 m/z = 724.90(C55H36N2 = 724.28) 155 m/z = 674.82(C51H34N2 =674.27) 156 m/z = 673.85(C52H35N = 673.27) 157 m/z = 749.95(C58H39N =749.30) 158 m/z = 750.94(C57H38N2 = 750.30) 159 m/z = 723.91(C56H37N =723.29) 160 m/z = 701.86(C53H35NO = 701.27) 161 m/z = 663.82(C49H33N3 =663.26) 162 m/z = 739.92(C55H37N3 = 739.29) 163 m/z = 647.75(C46H34NOP =647.23) 164 m/z = 697.81(C50H36NOP = 697.25) 165 m/z = 698.80(C49H35N2OP= 698.24) 166 m/z = 487.60(C35H25N3 = 487.20) 167 m/z = 397.52(C30H23N =397.18) 168 m/z = 398.50(C29H22N2 = 398.17) 169 m/z = 398.50(C29H22N2 =398.17) 170 m/z = 398.50(C29H22N2 = 398.17) 171 m/z = 447.58(C34H25N =447.19) 172 m/z = 448.56(C33H24N2 = 448.19) 173 m/z = 448.56(C33H24N2 =448.19) 174 m/z = 497.64(C38H27N = 497.21) 175 m/z = 649.83(C50H35N =649.27) 176 m/z = 521.66(C40H27N = 521.21) 177 m/z = 598.74(C45H30N2 =598.24) 178 m/z = 598.74(C45H30N2 = 598.24) 179 m/z = 499.61(C36H25N3 =499.20) 180 m/z = 575.71(C45H29N3 = 575.23) 181 m/z = 499.61(C36H25N3 =499.20) 182 m/z = 651.81(C48H33N3 = 651.26) 183 m/z = 521.66(C40H27N =521.21) 184 m/z = 547.70(C42H29N = 547.23) 185 m/z = 399.49(C28H21N3 =399.17) 186 m/z = 448.56(C33H24N3 = 448.19) 187 m/z = 497.64(C38H27N =497.21) 188 m/z = 651.81(C48H33N3 = 651.26) 189 m/z = 552.68(C39H28N4 =552.23) 190 m/z = 628.77(C45H32N4 = 628.26) 191 m/z = 704.87(C51H36N4 =704.29) 192 m/z = 704.87(C51H36N4 = 704.29) 193 m/z = 564.69(C40H28N4 =564.23) 194 m/z = 637.82(C49H35N = 637.27) 195 m/z = 635.81(C49H33N =635.26) 196 m/z = 514.67(C38H30N2 = 514.24) 197 m/z = 487.60(C35H25N3 =487.20) 198 m/z = 552.68(C39H28N4 = 552.23) 199 m/z = 474.60(C35H26N2 =474.21) 200 m/z = 474.60(C35H26N2 = 474.21) 201 m/z = 474.60(C35H26N2 =474.21) 202 m/z = 524.66(C39H28N2 = 524.22) 203 m/z = 524.66(C39H28N2 =524.22) 204 m/z = 575.71(C42H29N3 = 575.23) 205 m/z = 651.81(C48H33N3 =651.26) 206 m/z = 575.71(C42H29N3 = 575.23) 207 m/z = 727.91(C54H37N3 =727.29) 208 m/z = 627.79(C46H33N3 = 627.26) 209 m/z = 551.69(C40H29N3 =551.23) 210 m/z = 552.68(C39H28N4 = 552.23) 211 m/z = 551.69(C40H29N3 =551.23) 212 m/z = 551.69(C40H29N3 = 551.23) 213 m/z = 551.69(C40H29N3 =551.23) 214 m/z = 551.69(C40H29N3 = 551.23) 215 m/z = 651.81(C48H33N3 =651.26) 216 m/z = 651.81(C48H33N3 = 651.26) 217 m/z = 549.71(C42H31N =549.24) 218 m/z = 649.83(C50H35N = 649.27) 219 m/z = 749.95(C58H39N =749.30) 220 m/z = 1054.34(C82H55N = 1053.43) 221 m/z = 798.00(C62H39N =797.30) 222 m/z = 952.17(C72H45N3 = 951.26) 223 m/z = 952.17(C72H45N3 =952.36) 224 m/z = 753.90(C54H35N5 = 753.28) 225 m/z = 906.10(C66H43N5 =905.35) 226 m/z = 753.90(C54H35N5 = 753.28) 227 m/z = 1058.30(C78H51N5 =1057.41) 228 m/z = 551.69(C40H29N3 = 551.23) 229 m/z = 473.61(C36H27N =473.21) 230 m/z = 474.60(C35H26N2 = 474.21) 231 m/z = 474.60(C35H26N2 =474.21) 232 m/z = 474.60(C35H26N2 = 474.21) 233 m/z = 524.66(C39H28N2 =524.22) 234 m/z = 524.66(C39H28N2 = 524.22) 235 m/z = 575.71(C42H29N3 =575.23) 236 m/z = 701.87(C52H35N3 = 701.28) 237 m/z = 625.77(C46H31N3 =625.25) 238 m/z = 727.91(C54H37N3 = 727.29) 239 m/z = 523.67(C40H29N =523.23) 240 m/z = 573.73(C44H31N = 573.24) 241 m/z = 725.93(C56H39N =725.30) 242 m/z = 597.76(C46H31N = 597.24) 243 m/z = 674.84(C51H34N2 =674.27) 244 m/z = 674.84(C51H34N2 = 674.27) 245 m/z = 651.83(C48H33N3 =651.81) 246 m/z = 729.88(C52H35N5 = 729.28) 247 m/z = 627.79(C46H33N3 =627.26) 248 m/z = 551.69(C40H29N3 = 551.23) 249 m/z = 552.68(C39H28N4 =552.23) 250 m/z = 551.69(C40H29N3 = 551.23) 251 m/z = 602.74(C43H30N4 =602.24) 252 m/z = 628.77(C45H32N4 = 628.26 253 m/z = 627.79(C46H33N3 =627.26) 254 m/z = 486.61(C36H26N2 = 486.21) 255 m/z = 474.60(C35H26N2 =474.21) 256 m/z = 474.60(C35H26N2 = 474.21) 257 m/z = 474.60(C35H26N2 =474.21) 258 m/z = 524.66(C39H28N2 = 524.22) 259 m/z = 524.66(C39H28N2 =524.22) 260 m/z = 575.71(C42H29N3 = 575.23) 261 m/z = 651.81(C48H33N3 =651.26) 262 m/z = 575.71(C42H29N3 = 575.23) 263 m/z = 727.91(C54H37N3 =727.29) 264 m/z = 473.61(C36H27N = 473.21) 265 m/z = 474.60(C35H26N2 =474.21) 266 m/z = 474.60(C35H26N2 = 474.21) 267 m/z = 474.60(C35H26N2 =474.21) 268 m/z = 524.66(C39H28N2 = 524.22) 269 m/z = 524.66(C39H28N2 =524.22) 270 m/z = 575.71(C42H29N3 = 575.23) 271 m/z = 651.81(C48H33N3 =651.26) 272 m/z = 575.71(C42H29N3 = 575.23) 273 m/z = 727.91(C54H37N3 =727.29) 274 m/z = 589.74(C43H31N3 = 589.25) 275 m/z = 589.74(C43H31N3 =589.25) 276 m/z = 690.89(C52H38N2 = 690.30) 277 m/z = 690.89(C52H38N2 =690.30) 278 m/z = 625.77(C46H31N3 = 625.25) 279 m/z = 673.85(C52H35N =673.27) 280 m/z = 649.83(C50H35N = 649.27) 281 m/z = 524.66(C39H28N2 =524.22) 282 m/z = 525.65(C38H27N3 = 525.22) 283 m/z = 623.79(C48H33N =623.26) 284 m/z = 647.82(C50H33N = 647.26) 285 m/z = 574.74(C43H30N2 =574.24) 286 m/z = 601.75(C44H31N3 = 601.25) 287 m/z = 601.75(C44H31N3 =601.25) 288 m/z = 649.83(C50H35N = 649.27) 289 m/z = 651.81(C48H33N3 =651.26) 290 m/z = 753.94(C56H39N3 = 753.31) 291 m/z = 677.85(C50H35N3 =677.28) 292 m/z = 574.24(C43H30N2 = 574.24) 293 m/z = 523.67(C40H29N =523.23) 294 m/z = 678.83(C49H34N4 = 678.27) 295 m/z = 753.94(C56H39N3 =753.31) 296 m/z = 753.94(C56H39N3 = 753.31) 297 m/z = 753.94(C56H39N3 =753.31) 298 m/z = 754.93(C55H38N4 = 754.31) 299 m/z = 830.04(C62H43N3 =829.34) 300 m/z = 829.05(C63H44N2 = 828.35) 301 m/z = 830.04(C62H43N3 =829.34) 302 m/z = 831.03(C61H42N4 = 830.34) 303 m/z = 727.91(C54H37N3 =727.29) 304 m/z = 575.71(C42H29N3 = 575.23) 305 m/z = 575.71(C42H29N3 =575.23) 306 m/z = 651.81(C48H33N3 = 651.26) 307 m/z = 651.81(C48H33N3 =651.26) 308 m/z = 651.81(C48H33N3 = 651.26) 309 m/z = 475.59(C34H25N3 =475.20) 310 m/z = 476.58(C33H24N4 = 476.20) 311 m/z = 526.64(C37H26N4 =526.21) 312 m/z = 652.80(C47H32N4 = 652.26) 313 m/z = 599.73(C44H29N3 =599.23) 314 m/z = 721.90(C56H35N = 721.27) 315 m/z = 575.71(C42H29N3 =575.23) 316 m/z = 625.77(C46H31N3 = 625.25) 317 m/z = 625.77(C46H31N3 =625.25) 318 m/z = 674.84(C51H34N2 = 674.27) 319 m/z = 674.84(C51H34N2 =674.27) 320 m/z = 674.84(C51H34N2 = 674.27) 321 m/z = 624.78(C47H32N2 =624.25) 322 m/z = 623.79(C48H33N = 623.26) 323 m/z = 699.89(C54H37N =699.29) 324 m/z = 700.88(C53H36N2 = 700.28) 325 m/z = 673.85(C52H35N =673.27) 326 m/z = 651.80(C49H33NO = 651.25) 327 m/z = 613.76(C45H31N3 =613.25) 328 m/z = 689.86(C51H35N3 = 689.28) 329 m/z = 597.69(C42H32NOP =597.22) 330 m/z = 647.75(C46H34NOP = 647.23) 331 m/z = 648.74(C45H33N2OP= 648.23) 332 m/z = 437.54(C31H23N3 = 437.18) 333 m/z = 575.71(C42H29N3= 575.23) 334 m/z = 623.79(C48H33N = 623.26) 335 m/z = 625.77(C46H31N3 =625.25) 336 m/z = 727.91(C54H37N3 = 727.29) 337 m/z = 651.81(C48H33N3 =651.26) 338 m/z = 548.68(C41H28N2 = 548.22) 339 m/z = 497.64(C38H27N =497.21) 340 m/z = 652.80(C47H32N4 = 652.26) 341 m/z = 727.91(C54H37N3 =727.29) 342 m/z = 728.89(C53H36N4 = 728.29) 343 m/z = 727.91(C54H37N3 =727.29) 344 m/z = 727.91(C54H37N3 = 717.29) 345 m/z = 801.02(C61H42N2 =802.33) 346 m/z = 804.00(C60H41N3 = 803.33) 347 m/z = 804.00(C60H41N4 =803.33) 348 m/z = 804.99(C59H40N4 = 804.32) 349 m/z = 701.87(C52H35N3 =701.28) 350 m/z = 549.67(C40H27N3 = 549.22) 351 m/z = 549.67(C40H27N3 =549.22) 352 m/z = 625.77(C46H31N3 = 625.25) 353 m/z = 647.82(C50H33N =647.26) 354 m/z = 623.79(C48H33N = 623.26) 355 m/z = 498.62(C37H26N2 =492.21) 356 m/z = 499.61(C36H25N3 = 499.20) 357 m/z = 597.76(C46H31N =597.24) 358 m/z = 621.78(C48H31N = 621.24) 359 m/z = 548.68(C41H28N2 =548.22) 360 m/z = 575.71(C42H29N3 = 575.23) 361 m/z = 599.73(C44H29N3 =599.23) 362 m/z = 575.71(C42H29N3 = 575.23) 363 m/z = 623.79(C48H33N =623.26) 364 m/z = 625.77(C46H31N3 = 625.25) 365 m/z = 448.56(C33H24N2 =488.19) 366 m/z = 448.46(C33H24N2 = 448.19) 367 m/z = 498.62(C37H26N2 =498.21) 368 m/z = 648.80(C49H32N2 = 648.25) 369 m/z = 549.67(C40H27N3 =549.22) 370 m/z = 625.77(C46H31N3 = 625.25) 371 m/z = 449.55(C32H23N3 =449.18) 372 m/z = 547.70(C42H29N = 547.23) 373 m/z = 564.73(C42H32N2 =564.25) 374 m/z = 602.74(C43H30N4 = 602.24) 375 m/z = 625.77(C46H31N3 =625.25) 376 m/z = 701.87(C5235N3 = 701.28) 377 m/z = 601.75(C44H31N3 =601.25) 378 m/z = 602.74(C43H30N4 = 602.24) 379 m/z = 601.75(C44H31N3 =601.25) 380 m/z = 625.77(C46H31N3 = 635.25) 381 m/z = 701.87(C52H35N3 =701.28) 382 m/z = 601.75(C44H31N3 = 601.25) 383 m/z = 602.74(C43H30N4 =602.24) 384 m/z = 677.85(C50H35N3 = 677.28) 385 m/z = 647.75(C46H34NOP =647.23) 386 m/z = 697.81(C50H36NOP = 697.25) 387 m/z = 602.74(C43H30N4 =602.24) 388 m/z = 625.77(C46H31N3 = 625.25) 389 m/z = 701.87(C52H35N3 =701.28) 390 m/z = 625.77(C46H31N3 = 625.25) 391 m/z = 602.74(C43H30N4 =602.24) 392 m/z = 639.80(C47H33N3 = 639.26) 393 m/z = 740.95(C56H40N2 =740.31) 394 m/z = 740.95(C56H40H2 = 740.31) 395 m/z = 675.83(C50H33N3 =675.26) 396 m/z = 575.71(C42H29N3 = 575.23) 397 m/z = 673.85(C52H35N =673.27) 398 m/z = 804.00(C60H41N3 = 803.33) 399 m/z = 727.91(C54H37N3 =727.29) 400 m/z = 625.77(C46H31N3 = 625.25) 401 m/z = 777.97(C58H39N3 =777.31) 402 m/z = 739.92(C55H37N3 = 739.29)

Experimental Example Experimental Example 1 1) Manufacture of OrganicLight Emitting Device

A glass substrate on which ITO was coated as a thin film to a thicknessof 1500 Å was cleaned with distilled water and ultrasonic waves. Afterthe cleaning with distilled water was finished, the substrate wasultrasonic cleaned with solvents such as acetone, methanol and isopropylalcohol, then dried, and UVO treatment was carried out for 5 minutes ina UV cleaner using UV. After that, the substrate was transferred to aplasma cleaner (PT), and plasma treatment was carried out under vacuumfor removing ITO work function and remaining film, and the substrate wastransferred to a thermal deposition apparatus for organic deposition.

On the ITO transparent electrode (anode), organic materials were formedin a two-stack white organic light emitting diode (WOLED) structure. Asfor the first stack, a hole transfer layer was formed first by thermalvacuum depositing TAPC to a thickness of 300 Å. After forming the holetransfer layer, a light emitting layer was thermal vacuum depositedthereon as follows. The light emitting layer was deposited to 300 Å bydoping FIrpic in 8% as a blue phosphorescent dopant to TCzl, a host. Anelectron transfer layer was formed to 400 Å using TmPyPB, and then acharge generation layer was formed to 100 Å by doping Cs₂CO₃ in 20% to acompound described in the following Table 8.

As for the second stack, a hole injection layer was formed first bythermal vacuum depositing MoO₃ to a thickness of 50 Å. A hole transferlayer, a common layer, was formed by doping MoO₃ to TAPC in 20% andforming to 100 Å, and then depositing TAPC to 300 Å. After depositing alight emitting layer to 300 Å thereon by doping Ir(ppy)₃, a greenphosphorescent dopant, in 8% to TCzl, a host, an electron transfer layerwas formed to 600 Å using TmPyPB. Lastly, an electron injection layerwas formed on the electron transfer layer by depositing lithium fluoride(LiF) to a thickness of 10 Å, and then a cathode was formed on theelectron injection layer by depositing an aluminum (Al) cathode to athickness of 1,200 Å to manufacture an organic electroluminescentdevice.

Meanwhile, all the organic compounds required to manufacture the OLEDdevice were vacuum sublimation purified under 10⁻⁶ torr to 10⁻⁸ torr byeach material to be used in the OLED manufacture.

2) Driving Voltage and Light Emission Efficiency of OrganicElectroluminescent Device

For the organic electroluminescent devices manufactured as above,electroluminescent light emission (EL) characteristics were measuredusing M7000 manufactured by McScience Inc., and with the measurementresults, T₉₅ when standard luminance was 3,500 cd/m² was measured usinga lifetime test system (M6000) manufactured by McScience Inc. Results ofmeasuring a driving voltage, light emission efficiency, external quantumefficiency and a color coordinate (CIE) of the white organicelectroluminescent devices manufactured according to the presentdisclosure are as shown in Table 8.

TABLE 8 Light Driving Emission Voltage Efficiency CIE Lifespan Compound(V) (cd/A) (x, y) (T95) Example 1 1 8.13 60.17 (0.211, 27 0.434) Example2 6 7.41 64.86 (0.220, 33 0.480) Example 3 9 8.71 58.11 (0.223, 210.470) Example 4 10 8.03 62.27 (0.210, 25 0.424) Example 5 13 7.08 68.92(0.208, 45 0.420) Example 6 14 7.18 69.91 (0.207, 46 0.421) Example 7 157.01 69.32 (0.206, 45 0.419) Example 8 27 7.28 68.83 (0.205, 43 0.411)Example 9 32 7.05 68.52 (0.201, 42 0.416) Example 34 8.03 69.08 (0.215,34 10 0.425) Example 39 8.69 51.00 (0.212, 23 11 0.421) Example 44 7.6366.13 (0.211, 32 12 0.427) Example 53 8.25 55.92 (0.212, 25 13 0.391)Example 65 7.93 62.05 (0.234, 36 14 0.445) Example 70 8.30 52.00 (0.213,42 15 0.421) Example 72 7.12 67.56 (0.209, 44 16 0.415) Example 77 7.8661.19 (0.232, 22 17 0.443) Example 80 7.01 69.94 (0.209, 41 18 0.418)Example 82 7.31 50.11 (0.212, 23 19 0.421) Example 86 8.58 50.11 (0.211,25 20 0.417) Example 95 8.89 61.73 (0.209, 27 21 0.414) Example 104 8.7957.33 (0.212, 28 22 0.423) Example 105 8.67 58.91 (0.222, 29 23 0.413)Example 110 7.55 66.48 (0.208, 33 24 0.419) Example 113 7.87 62.86(0.229, 24 25 0.452) Example 117 7.74 62.25 (0.218, 25 26 0.443) Example120 8.12 59.34 (0.216, 24 27 0.483) Example 124 7.44 65.32 (0.207, 33 280.423) Example 125 8.89 57.91 (0.200, 35 29 0.423) Example 128 7.3465.77 (0.208, 31 30 0.418) Example 130 7.52 64.82 (0.210, 31 31 0.422)Example 138 7.53 66.12 (0.212, 30 32 0.429) Example 146 7.24 68.88(0.212, 40 33 0.423) Example 149 8.11 54.11 (0.212, 39 34 0.433) Example155 7.91 61.34 (0.211, 26 35 0.423) Example 160 7.72 64.31 (0.202, 26 360.422) Example 171 7.92 61.87 (0.222, 24 37 0.445) Example 174 7.9466.16 (0.229, 28 38 0.465) Example 176 8.42 51.84 (0.211, 22 39 0.413)Example 178 7.87 63.32 (0.206, 26 40 0.428) Example 179 7.21 69.93(0.209, 39 41 0.416) Example 184 8.08 62.24 (0.209, 25 42 0.423) Example187 7.91 58.99 (0.219, 33 43 0.421) Example 195 7.98 63.43 (0.209, 26 440.420) Example 196 7.86 61.81 (0.222, 25 45 0.434) Example 198 8.0056.99 (0.217, 32 46 0.411) Example 208 7.63 66.12 (0.212, 30 47 0.419)Example 209 8.21 59.00 (0.213, 27 48 0.423) Example 211 7.57 65.66(0.214, 29 49 0.426) Example 218 7.88 59.71 (0.207, 25 50 0.421) Example224 7.21 69.02 (0.208, 41 51 0.427) Example 226 7.05 68.22 (0.208, 43 520.421) Example 236 7.98 52.11 (0.212, 26 53 0.423) Example 248 7.1151.48 (0.221, 25 54 0.411) Example 261 8.22 50.95 (0.213, 22 55 0.413)Example 271 8.21 56.71 (0.211, 28 56 0.4033) Example 280 8.11 64.99(0.201, 26 57 0.421) Example 284 7.96 50.09 (0.217, 27 58 0.430) Example291 8.21 51.22 (0.202, 25 59 0.411) Example 298 7.51 66.10 (0.208, 28 600.418) Example 303 7.44 65.99 (0.211, 29 61 0.422) Example 316 7.9764.00 (0.228, 27 62 0.437) Example 320 8.01 60.11 (0.232, 25 63 0.441)Example 323 8.32 57.99 (0.210, 26 64 0.449) Example 328 7.38 59.31(0.211, 26 65 0.419) Example 329 8.21 59.77 (0.219, 27 66 0.426) Example332 7.44 65.33 (0.211, 32 67 0.429) Example 337 7.05 51.11 (0.221, 26 680.433) Example 341 8.01 51.02 (0.211, 24 69 0.421) Example 349 8.8960.12 (0.222, 27 70 0.427) Example 357 8.88 56.26 (0.218, 28 71 0.421)Example 360 8.91 52.23 (0.211, 24 72 0.411) Example 361 8.11 58.22(0.218, 31 73 0.422) Example 392 8.60 51.90 (0.208, 25 74 0.429) Example395 7.89 63.28 (0.209, 30 75 0.431) Example 399 8.11 56.90 (0.201, 21 760.429) Example 400 8.21 55.33 (0.217, 33 77 0.423) Example 401 8.6751.22 (0.209, 26 78 0.411) Example 402 8.55 50.11 (0.210, 21 79 0.429)Comparative TmPyPB 8.58 53.95 (0.212, 23 Example 1 0.433)

As shown from the results of Table 8, the organic electroluminescentdevices using the charge generation layer material of the 2-stack whiteorganic electroluminescent device of the present disclosure had a lowdriving voltage and improved light emission efficiency compared toComparative Example 1. Particularly, it was identified that Compounds13, 14, 15, 27, 32, 72, 80, 146, 179, 224, 226, 361 and 395 weresignificantly excellent in all of driving, efficiency and lifespan.

The presumed reason for such results is that the compound of the presentdisclosure used as an N-type charge generation layer formed with aninvented skeleton having proper length, strength and flat property and aproper hetero-compound capable of binding with metals is doped with analkali metal or an alkali-earth metal to form a gap state within theN-type charge generation layer, and electrons produced from a P-typecharge generation layer are readily injected to the electron transferlayer through the gap state produced within the N-type charge generationlayer. Accordingly, the P-type charge generation layer favorably carriedout electron injection and electron transfer to the N-type chargegeneration layer, and as a result, it is considered that a drivingvoltage of the organic light emitting device decreased, and efficiencyand lifespan were improved.

Experimental Example 2 1) Manufacture of Organic Light Emitting Device

A glass substrate on which ITO was coated as a thin film to a thicknessof 1500 Å was cleaned with distilled water and ultrasonic waves. Afterthe cleaning with distilled water was finished, the substrate wasultrasonic cleaned with solvents such as acetone, methanol and isopropylalcohol, then dried, and UVO treatment was carried out for 5 minutes ina UV cleaner using UV. After that, the substrate was transferred to aplasma cleaner (PT), and plasma treatment was carried out under vacuumfor removing ITO work function and remaining film, and the substrate wastransferred to a thermal deposition apparatus for organic deposition. Onthe ITO transparent electrode (anode), organic materials were formed ina single-stack structure. As a hole injection layer, HAT-CN wasdeposited to a thickness of 50 Å, and subsequently, a hole transferlayer was formed by doping DNTPD within 10% to NPD, depositing theresult to a thickness of 1500 Å, and continuously depositing TCTA to athickness of 200 Å. Subsequently, a light emitting layer comprising at-Bu-perylene dopant in an ADN host was formed to a thickness of 250 Å.Next, Alq₃, an electron transfer layer, was formed to a thickness of 250Å, and an N-type charge transfer layer was formed to a thickness of 100Å by doping Li, an alkali metal, to a compound described in thefollowing Table 9, and Al, a cathode, was formed to a thickness ofapproximately 1,000 Å to manufacture an organic electroluminescentdevice.

2) Driving Voltage and Light Emission Efficiency of OrganicElectroluminescent Device

For the organic electroluminescent devices manufactured as above,electroluminescent light emission (EL) characteristics were measuredusing M7000 manufactured by McScience Inc., and with the measurementresults, T₉₅ when standard luminance was 750 cd/m² was measured using alifetime test system (M6000) manufactured by McScience Inc. Results ofmeasuring a driving voltage, light emission efficiency, external quantumefficiency and a color coordinate (CIE) of the white organicelectroluminescent devices manufactured according to the presentdisclosure are as shown in Table 9.

TABLE 9 Light Driving Emission Voltage Efficiency CIE Lifespan Compound(V) (cd/A) (x, y) (T95) Example 1 5.89 6.12 (0.134, 26 80 0.108) Example6 4.99 6.53 (0.134, 31 81 0.102) Example 9 6.01 6.12 (0.134, 26 820.101) Example 10 5.99 6.00 (0.134, 24 83 0.108) Example 13 4.48 6.99(0.134, 44 84 0.099) Example 14 4.50 6.87 (0.134, 46 85 0.099) Example15 4.61 6.88 (0.134, 45 86 0.098) Example 27 4.55 6.89 (0.134, 42 870.098) Example 32 4.50 6.71 (0.134, 41 88 0.097) Example 34 5.02 6.51(0.134, 31 89 0.103) Example 39 5.76 4.21 (0.134, 29 90 0.108) Example44 5.23 6.61 (0.134, 33 91 0.103) Example 53 6.00 6.11 (0.134, 24 920.110) Example 65 5.09 6.67 (0.134, 35 93 0.105) Example 70 5.41 6.11(0.134, 28 94 0.106) Example 72 4.57 6.82 (0.134, 45 95 0.100) Example77 5.91 6.21 (0.134, 23 96 0.109) Example 80 4.48 6.91 (0.134, 44 970.098) Example 82 6.21 6.11 (0.134, 30 98 0.107) Example 86 5.70 6.00(0.134, 31 99 0.109) Example 95 5.81 6.12 (0.134, 33 100 0.110) Example104 6.09 6.09 (0.134, 31 101 0.111) Example 105 5.61 6.11 (0.134, 29 1020.101) Example 110 5.55 6.56 (0.134, 35 103 0.100) Example 113 5.99 6.07(0.134, 24 104 0.100) Example 117 5.88 6.14 (0.134, 26 105 0.105)Example 120 6.09 6.03 (0.134, 25 106 0.109) Example 124 4.79 6.77(0.134, 34 107 0.102) Example 125 5.88 6.01 (0.134, 26 108 0.108)Example 128 4.88 6.75 (0.134, 32 109 0.102) Example 130 4.90 6.78(0.134, 33 110 0.100) Example 138 4.78 6.77 (0.134, 32 111 0.101)Example 146 4.41 6.93 (0.134, 41 112 0.099) Example 149 5.89 5.94(0.134, 29 113 0.110) Example 155 5.81 6.16 (0.134, 27 114 0.110)Example 160 5.98 6.28 (0.134, 27 115 0.109) Example 171 5.66 6.34(0.134, 25 116 0.108) Example 174 5.58 6.18 (0.134, 29 117 0.109)Example 176 6.01 6.11 (0.134, 31 118 0.114) Example 178 5.77 6.11(0.134, 26 119 0.105) Example 179 4.50 6.90 (0.134, 42 120 0.100)Example 184 5.78 6.23 (0.134, 27 121 0.102) Example 187 5.89 4.91(0.134, 26 122 0.101) Example 195 5.79 6.19 (0.134, 28 123 0.109)Example 196 5.80 6.20 (0.134, 25 124 0.102) Example 198 5.88 6.11(0.134, 29 125 0.101) Example 208 5.01 6.60 (0.134, 31 126 0.101)Example 209 6.04 6.10 (0.134, 25 127 0.110) Example 211 5.29 6.50(0.134, 30 128 0.101) Example 218 5.89 6.33 (0.134, 27 129 0.109)Example 224 4.57 6.81 (0.134, 39 130 0.098) Example 226 4.54 6.87(0.134, 39 131 0.098) Example 236 5.91 5.21 (0.134, 25 132 0.110)Example 248 5.99 6.11 (0.134, 24 133 0.105) Example 261 6.09 5.41(0.134, 25 134 0.106) Example 271 6.13 5.23 (0.134, 26 135 0.101)Example 280 5.80 6.19 (0.134, 27 136 0.105) Example 284 5.99 6.09(0.134, 23 137 0.105) Example 291 5.98 6.01 (0.134, 31 138 0.106)Example 298 5.22 6.54 (0.134, 28 139 0.100) Example 303 5.02 6.65(0.134, 29 140 0.100) Example 316 5.81 6.23 (0.134, 22 141 0.105)Example 320 5.93 6.23 (0.134, 23 142 0.104) Example 323 5.92 6.22(0.134, 24 143 0.104) Example 328 5.87 4.28 (0.134, 23 144 0.101)Example 329 5.71 6.28 (0.134, 24 145 0.105) Example 332 5.21 6.52(0.134, 30 146 0.100) Example 337 5.21 6.11 (0.134, 23 147 0.110)Example 341 5.50 6.23 (0.134, 24 148 0.100) Example 349 5.51 6.09(0.134, 22 149 0.110) Example 357 5.60 6.11 (0.134, 23 150 0.104)Example 360 5.81 6.09 (0.134, 24 151 0.110) Example 361 5.33 6.33(0.134, 29 152 0.109) Example 392 5.40 6.10 (0.134, 25 153 0.110)Example 395 5.71 6.33 (0.134, 28 154 0.108) Example 399 5.51 6.01(0.134, 22 155 0.111) Example 400 5.33 6.12 (0.134, 26 156 0.107)Example 401 5.45 6.09 (0.134, 24 157 0.110) Example 402 5.70 6.23(0.134, 26 158 0.110) Comparative Bphen 5.82 6.23 (0.134, 27 Example 20.110)

As shown from the results of Table 9, the organic electroluminescentdevices using the charge generation layer material of the blue organicelectroluminescent device of the present disclosure had a low drivingvoltage and improved light emission efficiency compared to ComparativeExample 2. Particularly, it was identified that Compounds 13, 14, 15,27, 32, 72, 80, 146, 179, 224, 226, 361 and 395 were significantlyexcellent in all of driving, efficiency and lifespan.

The presumed reason for such results is that the compound of the presentdisclosure used as an N-type charge generation layer formed with aninvented skeleton having proper length, strength and flat property and aproper hetero-compound capable of binding with metals is doped with analkali metal or an alkali-earth metal to form a gap state within theN-type charge generation layer, and electrons produced from a P-typecharge generation layer are readily injected to the electron transferlayer through the gap state produced within the N-type charge generationlayer. Accordingly, the P-type charge generation layer favorably carriedout electron injection and electron transfer to the N-type chargegeneration layer, and as a result, it is considered that a drivingvoltage of the organic light emitting device decreased, and efficiencyand lifespan were improved.

Experimental Example 3 1) Manufacture of Organic Light Emitting Device

A transparent electrode ITO thin film obtained from glass for an OLED(manufactured by Samsung Corning Advanced Glass) was ultrasonic cleanedconsecutively using trichloroethylene, acetone, ethanol and distilledwater for 5 minutes each, placed in isopropanol and stored, and thenused.

Next, the ITO substrate was installed in a substrate folder of vacuumdeposition equipment, and the following4,4′,4″-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine (2-TNATA) wasintroduced to a cell in the vacuum deposition equipment.

Subsequently, the chamber was exhausted until the degree of vacuuminside the chamber reached 10⁻⁶ torr, and then a current was applied tothe cell to evaporate the 2-TNATA to deposit a hole injection layerhaving a thickness of 600 Å on the ITO substrate.

The following N,N′-bis(α-naphthyl)-N,N′-diphenyl-4,4′-diamine (NPB) wasintroduced to a different cell in the vacuum deposition equipment, acurrent was applied to the cell to evaporate to deposit a hole transferlayer having a thickness of 300 Å on the hole injection layer.

After forming the hole injection layer and the hole transfer layer asabove, a blue light emitting material having a structure as follows wasdeposited thereon as a light emitting layer. Specifically, H1, a bluelight emitting host material, was vacuum deposited to a thickness of 200Å on one cell in the vacuum deposition equipment, and D1, a blue lightemitting dopant material, was vacuum deposited thereon in 5% withrespect to the host material.

Subsequently, a compound of the following structural formula E1 wasdeposited to a thickness of 300 Å as an electron transfer layer.

As an electron injection layer, lithium fluoride (LiF) was deposited toa thickness of 10 Å, and an Al cathode was formed to a thickness of 1000Å to manufacture an OLED device.

Meanwhile, all the organic compounds required to manufacture the OLEDdevice were vacuum sublimation purified under 10⁻⁶ torr to 10⁻⁸ torr byeach material to be used in the OLED manufacture.

2) Driving Voltage and Light Emission Efficiency of OrganicElectroluminescent Device

For the organic electroluminescent devices manufactured as above,electroluminescent light emission (EL) characteristics were measuredusing M7000 manufactured by McScience Inc., and with the measurementresults, T₉₅ when standard luminance was 700 cd/m² was measured using alifetime test system (M6000) manufactured by McScience Inc. Results ofmeasuring a driving voltage, light emission efficiency, external quantumefficiency and a color coordinate (CIE) of the white organicelectroluminescent devices manufactured according to the presentdisclosure are as shown in Table 10.

TABLE 10 Light Driving Emission Voltage Efficiency CIE Lifespan Compound(V) (cd/A) (x, y) (T95) Example 1 4.48 7.01 (0.134, 40 159 0.098)Example 6 5.01 6.59 (0.134, 36 160 0.100) Example 9 5.89 5.78 (0.134, 31161 0.100) Example 10 4.50 7.11 (0.134, 41 162 0.099) Example 13 5.556.02 (0.134, 29 163 0.105) Example 14 5.49 6.00 (0.134, 31 164 0.101)Example 15 5.33 5.89 (0.134, 29 165 0.102) Example 27 5.49 5.98 (0.134,28 166 0.100) Example 32 5.50 6.22 (0.134, 30 167 0.100) Example 34 5.006.75 (0.134, 36 168 0.100) Example 39 6.23 6.01 (0.134, 31 169 0.102)Example 44 5.01 6.62 (0.134, 36 170 0.101) Example 53 4.52 6.90 (0.134,42 171 0.100) Example 65 5.11 6.62 (0.134, 37 172 0.102) Example 70 5.006.01 (0.134, 31 173 0.100) Example 72 5.63 5.88 (0.134, 32 174 0.105)Example 77 4.39 6.99 (0.134, 40 175 0.100) Example 80 5.48 6.01 (0.134,31 176 0.105) Example 82 5.67 6.05 (0.134, 31 177 0.101) Example 86 5.515.97 (0.134, 29 178 0.102) Example 95 5.54 5.96 (0.134, 34 179 0.100)Example 104 5.31 5.67 (0.134, 29 180 0.103) Example 105 5.22 5.94(0.134, 30 181 0.101) Example 110 4.90 6.67 (0.134, 40 182 0.101)Example 113 4.35 7.17 (0.134, 41 183 0.099) Example 117 4.51 7.09(0.134, 42 184 0.098) Example 120 4.44 7.15 (0.134, 42 185 0.099)Example 124 4.98 6.38 (0.134, 37 186 0.101) Example 125 5.50 5.67(0.134, 29 187 0.101) Example 128 5.02 6.76 (0.134, 35 188 0.100)Example 130 5.05 6.45 (0.134, 36 189 0.099) Example 138 5.16 6.66(0.134, 36 190 0.100) Example 146 6.22 6.09 (0.134, 28 191 0.105)Example 149 5.88 5.99 (0.134, 33 192 0.101) Example 155 4.39 7.02(0.134, 40 193 0.100) Example 160 4.40 7.21 (0.134, 44 194 0.099)Example 171 4.55 7.12 (0.134, 41 195 0.100) Example 174 4.53 6.97(0.134, 42 196 0.099) Example 176 5.61 6.13 (0.134, 31 197 0.100)Example 178 4.42 7.32 (0.134, 42 198 0.100) Example 179 5.56 6.11(0.134, 29 199 0.102) Example 184 4.44 7.21 (0.134, 40 200 0.099)Example 187 5.68 6.14 (0.134, 32 201 0.100) Example 195 4.49 7.09(0.134, 41 202 0.100) Example 196 4.51 6.99 (0.134, 40 203 0.099)Example 198 5.59 6.11 (0.134, 31 204 0.099) Example 208 4.82 6.75(0.134, 35 205 0.100) Example 209 5.83 5.90 (0.134, 31 206 0.100)Example 211 4.97 6.49 (0.134, 35 207 0.101) Example 218 4.55 6.96(0.134, 39 208 0.099) Example 224 5.49 6.00 (0.134, 32 209 0.100)Example 226 5.60 5.98 (0.134, 31 210 0.102) Example 236 5.88 5.71(0.134, 36 211 0.102) Example 248 5.59 5.99 (0.134, 32 212 0.100)Example 261 5.66 5.28 (0.134, 31 213 0.101) Example 271 5.78 5.67(0.134, 33 214 0.099) Example 280 4.55 7.05 (0.134, 40 215 0.100)Example 284 4.41 7.16 (0.134, 40 216 0.099) Example 291 5.71 6.01(0.134, 27 217 0.100) Example 298 5.11 6.75 (0.134, 37 218 0.102)Example 303 4.88 6.82 (0.134, 38 219 0.100) Example 316 4.49 7.00(0.134, 40 220 0.099) Example 320 4.38 7.02 (0.134, 44 221 0.098)Example 323 4.50 7.03 (0.134, 41 222 0.099) Example 328 5.87 5.98(0.134, 33 223 0.100) Example 329 4.59 7.17 (0.134, 42 224 0.098)Example 332 4.99 6.60 (0.134, 35 225 0.100) Example 337 5.99 5.01(0.134, 44 226 0.098) Example 341 5.58 5.00 (0.134, 41 227 0.099)Example 349 5.50 5.99 (0.134, 28 228 0.100) Example 357 5.94 5.60(0.134, 35 229 0.100) Example 360 5.57 5.77 (0.134, 31 230 0.100)Example 361 5.56 5.90 (0.134, 32 231 0.100) Example 392 5.46 5.22(0.134, 44 232 0.100) Example 395 5.91 5.88 (0.134, 37 233 0.098)Example 399 5.48 5.88 (0.134, 38 234 0.100) Example 400 5.21 5.61(0.134, 30 235 0.100) Example 401 5.99 5.00 (0.134, 32 236 0.099)Example 402 5.66 5.90 (0.134, 33 237 0.098) Comparative E1 5.56 5.91(0.134, 30 Example 3 0.100)

As shown from the results of Table 10, the organic electroluminescentdevices using the electron transfer layer material of the blue organicelectroluminescent device of the present disclosure had a low drivingvoltage and significantly improved light emission efficiency andlifespan compared to Comparative Example 3. Particularly, it wasidentified that Compounds 1, 10, 53, 77, 113, 117, 120, 155, 166, 171,174, 178, 184, 195, 196, 218, 280, 284, 316, 320, 323 and 329 weresignificantly excellent in all of driving, efficiency and lifespan.

The presumed reason for such results is that, when the invented compoundhaving proper length, strength and flat property is used as an electrontransfer layer, a compound in an excited state is produced by receivingelectrons under a specific condition, and particularly, when the excitedstate is formed in the heteroskeleton site of the compound, excitedenergy moves to a stable state before the excited heteroskeleton sitegoes through a different reaction, and the relatively stabilizedcompound is capable of efficiently transferring electrons withoutcompound decomposition or destruction. As a reference, it is consideredthat those having a stable state when excited are aryl or acene seriescompounds or multicyclic hetero-compounds. Accordingly, it is consideredthat the compound of the present disclosure enhances electron-transportproperties or improved stability resulting in excellency in all ofdriving, efficiency and lifespan.

1. A hetero-cyclic compound represented by the following ChemicalFormula 1:

wherein, in Chemical Formula 1, L1 is a direct bond; a substituted orunsubstituted C₆ to C₆₀ arylene group; or a substituted or unsubstitutedC₂ to C₆₀ heteroarylene group; Z1 is selected from the group consistingof hydrogen; deuterium; a halogen group; —CN; a substituted orunsubstituted C₁ to C₆₀ alkyl group; a substituted or unsubstituted C₆to C₆₀ aryl group; a substituted or unsubstituted C₂ to C₆₀ heteroarylgroup; —SiRR′R″; —P(═O)RR′; and an amine group unsubstituted orsubstituted with a C₁ to C₂₀ alkyl group, a C₆ to C₆₀ aryl group or a C₂to C₆₀ heteroaryl group; m is an integer of 0 to 4; n is an integer of 1to 4; R1 to R8 are the same as or different from each other, and eachindependently selected from the group consisting of hydrogen; deuterium;a halogen group; —CN; a substituted or unsubstituted C₁ to C₆₀ alkylgroup; a substituted or unsubstituted C₂ to C₆₀ alkenyl group; asubstituted or unsubstituted C₂ to C₆₀ alkynyl group; a substituted orunsubstituted C₁ to C₆₀ alkoxy group; a substituted or unsubstituted C₃to C₆₀ cycloalkyl group; a substituted or unsubstituted C₂ to C₆₀heterocycloalkyl group; a substituted or unsubstituted C₆ to C₆₀ arylgroup; a substituted or unsubstituted C₂ to C₆₀ heteroaryl group;—SiRR′R″; —P(═O)RR′; and an amine group unsubstituted or substitutedwith a C₁ to C₂₀ alkyl group, a C₆ to C₆₀ aryl group or a C₂ to C₆₀heteroaryl group, or two or more groups adjacent to each other bond toeach other to form a substituted or unsubstituted aliphatic or aromatichydrocarbon ring; and R, R′ and R″ are the same as or different fromeach other, and each independently hydrogen; deuterium; —CN; asubstituted or unsubstituted C₁ to C₆₀ alkyl group; a substituted orunsubstituted C₃ to C₆₀ cycloalkyl group; a substituted or unsubstitutedC₆ to C₆₀ aryl group; or a substituted or unsubstituted C₂ to C₆₀heteroaryl group.
 2. The hetero-cyclic compound of claim 1, whereinChemical Formula 1 is represented by any one of the following ChemicalFormulae 2 to 7:

wherein, in Chemical Formulae 2 to 7, R9 is represented by -(L2)p-(Z2)q;L2 has the same definition as L1 of Chemical Formula 1 and Z2 has thesame definition as Z1 of Chemical Formula 1; p is an integer of 0 to 3;q is an integer of 1 to 4; and R1 to R8 have the same definitions as inChemical Formula
 1. 3. The hetero-cyclic compound of claim 1, wherein Z1is selected from the group consisting of hydrogen; deuterium; asubstituted or unsubstituted C₆ to C₆₀ aryl group; a substituted orunsubstituted C₂ to C₆₀ heteroaryl group; and —P(═O)RR′, and R, R′ andR″ are the same as or different from each other and each independentlyhydrogen; deuterium; —CN; a substituted or unsubstituted C₁ to C₆₀ alkylgroup; a substituted or unsubstituted C₃ to C₆₀ cycloalkyl group; asubstituted or unsubstituted C₆ to C₆₀ aryl group; or a substituted orunsubstituted C₂ to C₆₀ heteroaryl group.
 4. The hetero-cyclic compoundof claim 1, wherein R1 and R2 bond to each other to form an aromatichydrocarbon ring, or R3 and R4 bond to each other to form an aromatichydrocarbon ring, and, among R1 to R4, groups that do not form thearomatic hydrocarbon ring are hydrogen or deuterium, and R5 to R8 areeach independently hydrogen or deuterium.
 5. The hetero-cyclic compoundof claim 1, wherein Chemical Formula 1 is represented by any one of thefollowing compounds:


6. An organic light emitting device comprising: an anode; a cathode; andone or more organic material layers provided between the anode and thecathode, wherein one or more layers of the organic material layerscomprise the hetero-cyclic compound of claim
 1. 7. The organic lightemitting device of claim 6, wherein the organic material layer comprisesat least one of a hole blocking layer, an electron injection layer andan electron transfer layer, and at least one of the hole blocking layer,the electron injection layer and the electron transfer layer comprisesthe hetero-cyclic compound.
 8. The organic light emitting device ofclaim 6, wherein the organic material layer comprises a light emittinglayer, and the light emitting layer comprises the hetero-cycliccompound.
 9. The organic light emitting device of claim 6, wherein theorganic material layer comprises one or more of a hole injection layer,a hole transfer layer, and a layer carrying out hole injection and holetransfer at the same time, and one of the above-mentioned layerscomprises the hetero-cyclic compound.
 10. The organic light emittingdevice of claim 6, wherein the organic material layer comprises a chargegeneration layer, and the charge generation layer comprises thehetero-cyclic compound.
 11. The organic light emitting device of claim6, comprising: an anode; a first stack provided on the anode andcomprising a first light emitting layer; a charge generation layerprovided on the first stack; a second stack provided on the chargegeneration layer and comprising a second light emitting layer; and acathode provided on the second stack.